N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine
Camptothecine
CAS: 7689-03-4
Molecular Formula: C20H16N2O4
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Names and Identifiers
| Name | Camptothecine |
| Synonyms | CaMpathecin Campothecin Camptothecin Camptothccin CaMpetothecin Camptothecine (+)-Camptothecin (20S)-CAMPTOTHECIN CaMptothecin(NATURAL) 1,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE 5,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE Camptothecin, Camptotheca acuminata N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine |
| CAS | 7689-03-4 |
| EINECS | 444-280-6 |
| InChI | InChI=1/C16H23N5O4/c22-6-10-12(23)13(24)16(25-10)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h7-10,12-13,16,22-24H,1-6H2,(H,17,18,20) |
| InChIKey | VSJKWCGYPAHWDS-FQEVSTJZSA-N |
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Physico-chemical Properties
| Molecular Formula | C20H16N2O4 |
| Molar Mass | 348.35 |
| Density | 1.3112 (rough estimate) |
| Melting Point | 260°C (dec.)(lit.) |
| Boling Point | 482.73°C (rough estimate) |
| Specific Rotation(α) | D25 +31.3° (in chloroform-methanol, 8:2) |
| Flash Point | 362.1°C |
| Water Solubility | insoluble |
| Solubility | chloroform/methanol (4:1): 4mg/mL |
| Vapor Presure | 3.74E-19mmHg at 25°C |
| Appearance | Solid |
| Color | yellow |
| Merck | 14,1735 |
| BRN | 631069 |
| pKa | pKa 10.83 (Uncertain) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| Refractive Index | 1.5700 (estimate) |
| MDL | MFCD00081076 |
| Physical and Chemical Properties | Melting point 260°C water-soluble insoluble |
| Use | For the treatment of gastric cancer, colorectal cancer, chronic granulocyte type and acute leukemia |
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R25 - Toxic if swallowed R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| UN IDs | UN 1544 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UQ0492000 |
| HS Code | 29399990 |
| Hazard Note | Irritant |
| Hazard Class | 6.1 |
| Packing Group | Ⅲ |
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Reference
| Reference Show more | 1. Guo Weihang, Chen Song, Wang Xianheng et al. Preparation of 20(S)-camptothecin ester intermediates [J]. Journal of Zunyi Medical University 2019 v.42;No.193(06):55-58. 2. Liu Weifen and Yunlin, Yin Li, etc. Determination of hydroxycamptothecin in blood and tissue samples by HPLC-fluorescence [J]. Journal of Henan University (Medical Sciences) 2018 037(003):159-162 165. 3. Yu Lili, Wei Yuanyuan, Liu Qian, et al. Synthesis and properties of RGD modified Camptothecin-loaded particles [J]. New Chemical Materials 2017(12). 4. Li Hongying, long Lan, Li Yajie, et al. Selection of HPLC methods for extracting camptothecin from young leaves of Camptotheca acuminata [J]. Journal of Hubei University for Nationalities (self-Science Edition) 2012 000(002):139-141. 5. Li Chao, Li Jing, Li Xingchi et al. Effect of camptothecin on acute lung injury induced by LPS [J]. Veterinary science in China, 2020 v.50;No.509(01):132-138. 6. Tan Huanhuan, Xing Zhihua, Shen Yun, et al. Preparation and characterization of hydroxycamptothecin chitosan nano lyophilized powder [J]. Journal of Harbin University of Commerce (natural sciences edition), 2014, 000(001):13-17. 7. Fan Sufang, Ma Junmei, Liu Min, et al. Determination of 15 toxic alkaloids in foods by high performance liquid chromatography-tandem mass spectrometry [J]. Food Science, 2018, 39(22):290-295. 8. Yang Jianhang, Zhao Xiaohua. Extraction of Camptothecin and hydroxycamptothecin from Camptotheca acuminata leaves by micelle-mediated method combined with ultrasonic-microwave-assisted method [J]. Journal of Plant Research, 2020,40(06):951-960. 9. [IF = 2.87] Yu Lili et al."Photo-responsive polymeric micells bearing ammonia salts cross-linked for effective drug delivery." Polym Bull. 2019 May;76(5):2215-2231 |
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Introduction
Slightly soluble in ethanol and chloroform, hardly soluble in water. It cannot form a stable salt with acid, and can be heated and reacted with sodium hydroxide solution to form sodium salt and dissolve in water. Sodium salt aqueous solution yellow clear with blue fluorescence
Last Update：2022-10-16 17:28:34
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Pharmacology
Open Data Unverified Data
Camptothecine is a plant alkaloid primarily found in Huperzia serrata, a species of clubmoss plant. It has various pharmacological effects, including:
1. Sedative and hypnotic effects: Camptothecine has mild sedative and hypnotic effects, promoting sleep and relieving anxiety and tension.
2. Antidepressant effects: Studies have shown that Camptothecine can regulate neurotransmitter release, exhibiting antidepressant effects and alleviating symptoms of depression.
3. Anti-inflammatory effects: Camptothecine has anti-inflammatory properties, able to suppress inflammation and alleviate symptoms of inflammatory-related diseases.
4. Antioxidant effects: Camptothecine possesses antioxidant properties, scavenging free radicals to reduce oxidative stress and delay the aging process.
In conclusion, Camptothecine has multiple pharmacological effects and can be used in the treatment of anxiety, depression, inflammation, and as a general health supplement. However, it is important to note that research on Camptothecine is still ongoing, and specific applications and dosages should be supported by further clinical studies. When using Camptothecine, it is advisable to follow medical advice and avoid misuse to prevent adverse reactions.
Last Update：2024-04-09 19:43:38
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - camptothecin derivatives
Open Data Unverified Data
Representative drugs of Camptothecine derivatives include:
1. Vinblastine and Vincristine: These two Camptothecine derivatives are commonly used anti-cancer drugs in clinical practice, mainly used in the treatment of leukemia, lymphoma, and other malignant tumors.
2. Docetaxel and Paclitaxel: These two Camptothecine derivatives are widely used chemotherapy drugs for the treatment of various solid tumors such as breast cancer, ovarian cancer, and prostate cancer.
3. Pemetrexed: This is a folate metabolism inhibitor with anti-tumor and antiviral activities, mainly used in the treatment of non-small cell lung cancer and mesothelioma.
4. Ixabepilone: This is a microtubule stabilizer used to treat chemotherapy-resistant breast cancer and ovarian cancer.
These Camptothecine derivative drugs have been widely used in clinical practice for the treatment of various cancers and other diseases, highlighting the important role and potential of Camptothecine derivatives in the field of medicine.
Last Update：2024-04-09 19:43:38
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Poisoning
Open Data Unverified Data
Symptoms of Camptothecine poisoning include nausea, vomiting, headache, sweating, increased heart rate, low blood pressure, and in severe cases, may lead to coma, seizures, and life-threatening conditions.
If someone is suspected of Camptothecine poisoning, they should be immediately taken to the hospital for treatment. During first aid, it is important to keep the airway clear, maintain body temperature, and try to keep the person conscious. Medical professionals will provide appropriate care and treatment based on the symptoms, such as gastric lavage, administration of antidotes, etc.
To prevent Camptothecine poisoning, it is crucial to strictly follow the doctor's prescription and advice when taking medication. Avoid overdosing and do not adjust the medication dosage without medical guidance. Regular follow-up appointments and seeking medical attention promptly if unusual symptoms occur are also important for prevention.
Last Update：2024-04-09 19:43:38
N-cyclohexyl-9-pentofuranosyl-9H-purin-6-amine - Reference Information
| alkaloid | camptothecin is an alkaloid proposed from the seed or root bark of the deciduous plant Camptotheca acuminata, can directly destroy the DNA structure and DNA binding and make DNA susceptible to endonuclease Aggression, while inhibiting DNA polymerase and affect DNA replication, mainly sensitive to proliferating cells, cell cycle specific drugs, S phase, the G1, G2 and M phase cells have a slight lethality. It has inhibitory effect on a variety of animal tumors, and has no cross resistance to commonly used anti-tumor drugs. It can reduce toxicity without reducing curative effect when combined with glycyrrhizin. The mechanism of topical treatment of psoriasis is to inhibit the mitosis of keratinocytes with rapid division, to thin the spinous cell layer with hyperplasia, to disappear the parakeratosis, and to restore the formation of the granular layer to achieve the therapeutic effect. after intravenous injection, most drugs bind to plasma protein, and the Half-Life in plasma, kidney and liver is 30 minutes, with the highest content in gastrointestinal tract, bone marrow and kidney. This product excretion is slow, mainly in the original form of urinary excretion, 48 hours can be discharged 17%. It is mainly used for gastric cancer, colon cancer, rectal cancer, head and neck cancer and bladder cancer. |
| indications | is mainly used for gastrointestinal tumors, and has good curative effect on gastric cancer, rectal cancer and colon cancer, can improve the chance of advanced gastric cancer resection. It has certain curative effect on head and neck cylindrical adenocarcinoma, bladder cancer and lung adenocarcinoma. For primary liver cancer can make the tumor shrink, intravenous injection of camptothecin emulsion can increase the chance of liver cancer resection, malignant hydatidiform mole and choriocarcinoma also effective. Antitumor alkaloids. Irreversibly binds to the DNA-topoisomerase I complex, inhibits DNA re-binding following cleavage of topoisomerase I, and causes the enzyme to form a covalent linkage with the DNA. A cytotoxic antitumor drug. |
| usage and dosage | 1. Oral: each 5mg, 2 times a day, 0.5g for a course of treatment, generally used as maintenance therapy. 2. Intramuscular injection: 5mg each time, 1~2 times a day, 0.14 ~ 0.2g for a course of treatment. 3. Intravenous injection: 10mg each time, 1 times a day; Or 20mg each time, 1 times every other day; Or 30mg each time, 2 times a week, all diluted with normal saline 20ml, 1~0.2g for a course of treatment, the interval of treatment course should be several months; Suspension injection 5mg each time, diluted with glucose injection for intravenous injection, 2 times a week, 0.05~0.1g for a course of treatment. 4. Intravenous drip: 20mg each time, plus normal saline 250ml, once every other day, a course of 7~10 days. Arterial injection: hepatic artery or gastroepiploic artery cannulation, daily or every other day injection of 10mg plus normal saline 20ml, once a week. 5. Intratumoral injection: 5~10mg every day or once every other day. 6. Bladder perfusion: 20mg each time, plus normal saline 20ml, 1 times a day, 3 days for a course of treatment; Or 30~40mg each time, plus normal saline 50ml, 2 times a week, 4 weeks for a course of treatment. |
| clinical evaluation | camptothecin has been used to treat more than 1000 cases of tumor patients in China, indicating that the short-term effect on gastric cancer is better. But the remission period is short, only 2~3 months. It also has certain curative effect on cylindrical adenocarcinoma of head and neck, intestinal cancer and bladder cancer, can improve the chance of surgical resection for advanced gastric cancer, and is also effective for choriocarcinoma and leukemia. In fever, relieve pain, improve the general condition of patients, this product has a certain role. This information was edited by chemical book Xiaonan (2015-09-08). |
| camptothecin poisoning | camptothecin has strong irritation to mucosa, so gastrointestinal reaction and urinary tract irritation are the most common toxicity, myelosuppression was mainly leukopenia and thrombocytopenia. [poisoning] mainly gastrointestinal reactions, manifested as loss of appetite, Nausea, Vomit, Diarrhea; Severe cases, can cause electrolyte disorders. Urinary system reaction was frequent micturition, urgency, dysuria and hematuria. Cystoscopy showed mucosal congestion and small bleeding spots. Myelosuppression, mainly leukopenia and thrombocytopenia, occurs when the dosage of 100 ~ 140mg. [poisoning treatment] in case of severe urinary system reaction, the drug should be stopped immediately, and the patient should be encouraged to drink more water, rehydration and diuresis, and dilute the concentration of camptothecin in urine as much as possible. Application of sodium bicarbonate 0.5~1.0g, 3 times a day oral, to alkalinize urine. Have obvious hematuria, available hemostatic drugs. Or with 0.5% procaine for bilateral renal capsule closure. For the treatment of the remaining toxic reactions, see "intoxication with nitrogen mustard". [poisoning prevention] strictly control the dosage. During medication should drink more water, and oral sodium bicarbonate to reduce bladder irritation. Renal damage, urinary tract infection should be used with caution. It is suggested that hydroxycamptothecin (OPT) is a derivative of camptothecin, and its mechanism of action and anticancer spectrum are the same as camptothecin. After entering the body, OPT is mainly excreted from the biliary tract through feces, therefore, urinary system toxicity is rare. |
| adverse reactions | 1. Can cause hematuria, frequent urination, urgency and other urinary system symptoms, mostly in the use of 100 ~ 140mg appear; Generally sustainable for several weeks, should be immediately discontinued; Drink more tea to increase urine output, then its toxic reaction to the bladder is reduced. 2. Myelosuppression, but less severe. 3. Can cause more serious Diarrhea, there is loss of appetite, Nausea, etc., in severe cases can cause intestinal paralysis, and electrolyte disorders. 4. A few people have hair loss phenomenon. |
| precautions | 1. Alkalizing urine with sodium bicarbonate and drinking more water can reduce urinary tract toxicity, renal insufficiency or urinary tract infection slow use. 2, can be used to improve the hemogram of Chinese and Western medicine such as reserpine, caulis spatholobi, Polygonatum cuspidatum, etc. Diarrhea, the patient was stopped promptly and given symptomatic treatment. 4, white blood cells to 2 × 109/L should be discontinued, pregnant women should not use. 5, this product can not be diluted with glucose solution and acidic drug solution, should be diluted with normal saline. Injection immediately after dilution, not suitable for long time. |
| camptothecin derivatives | the main representative drugs of camptothecin derivatives are Topotecan (TPT) and Irinotecan (Irinotecan), CPT-11), has been studied and used in clinic. Topotecan (9-dimethylaminoethane-10-hydroxy-hexine hydrochloride) is a DNA topoisomerase I inhibitor, is a semi-synthetic, water-soluble natural camptothecin derivatives, when dissolved in normal saline, the lactone ring in its structure is hydrolyzed into a hydroxy acid that opens the ring, and the two form a dynamic equilibrium. The anticancer activity of the lactone type is much higher than that of the hydroxy acid, and the hydroxy acid type is the main form existing in the blood, when the blood pH 2~4 with ester type. Its anti-cancer mechanism is to prevent the repair of topoisomerase I, the role of breaking DNA, in the absence of topoisomerase, DNA replication in the process of rapid double helix helix, in theory, it will lead to an increase in the degree of helix of the double helix structure before the replication fork, and this increase in torque will make the subsequent transcription and replication process no longer possible. However, topoisomerases pass through intact DNA strands by generating reversible complexes with DNA and introducing transient enzyme-mediated cleavage of topoisomerase I and topoisomerase II. To reduce this torque. Through this mechanism it is possible to produce a continuous repair process. Topotecan acts by forming a stable covalent complex with a DNA-topoisomerase I polymer, which is why topotecan is cytotoxic, its inhibitory effect on topoisomerase I is mainly in the S phase, because the stable "cleavable complex" blocks the loosening and replication of DNA, and DNA strand breaks and DNA synthesis stops, S phase cells are irreversibly damaged, in addition, the replication fork is also damaged; Interrupt the DNA transcription process, and finally, lead to apoptosis and death, in vitro studies suggest that important factors for topotecan cytotoxic activity may be related to intracellular concentration and length of exposure. The pharmacokinetics was linear, and the proportional increase of the area under the concentration-time curve in plasma and the proportional increase of the peak value and steady-state concentration in plasma after higher dose were all the same, its distribution and metabolism belong to two-compartment model, and its pharmacokinetic parameters such as peak concentration and area under the curve are proportional to dose and related to hematological toxicity. Its tissue distribution is fast, and the average cerebrospinal fluid penetration is more than 30%. 30-minute intravenous infusion method, the elimination half-life of 3 hours, its excretion from the kidney 30% ~ 60%,12 hours after 90% of the drug is cleared, and in the bile and pleural fluid concentration and plasma equivalent: poor renal function in patients with dose should be adjusted, such as serum creatinine clearance rate ≥ 40ml/min does not have to change the dose, 20~39 ml/min, the dose should be reduced by 50%; No dose adjustment is required when blood bilirubin is> 25.5 μmol/L and <170 μmol/L. Irinotecan is another water-soluble derivative of camptothecin, in vivo by the role of carboxylesterase to remove pyridyl, pyridine carbonyl into metabolites SN-38 and play an anti-tumor effect, SN-38, the effect on tumor cells was 100 times stronger than that of irinotecan. Irinotecan inhibits DNA topoisomerase I, which plays a very important role in chromatin organization, mitosis, DNA replication, recombination and transcription, it does not require an energy supply, first of all through the phosphate bond with the DNA, the formation of the fracture of the complex, usually can be broken and non-covalent bond of the non-cleavable complex to form a balance, irinotecan shifts the equilibrium in the direction of the cleavable complex, causing single-strand breaks. This product has a wide anti-tumor spectrum, and the activity of inhibiting cell reproduction in vitro is weak, but the activity of its metabolite SN-38 is the same or stronger than that of ADM. L1210, P388, S180, MethA, 3 LL, B16 and rat tumor cell lines CO-4, MX-1, QG-56, ST15, SC-6 have good anti-tumor effect, vincristine, doxorubicin, the combined use of cisplatin, etoposide, fluorouracil and the like can enhance the anti-tumor effect and has no cross-resistance to existing anti-tumor drugs. |
| Use | anticancer drug. For gastric cancer, colon cancer, rectal cancer, head and neck cylindrical tumor type cancer and bladder cancer. for the treatment of gastric cancer, colorectal cancer, chronic granulocytic and acute leukemia, etc. irreversibly binds to DNA topoisomerase I complex, effects on cell cycle progression camptothecin was originally isolated from the stem of Camptotheca acuminata and exhibited anti-leukemic/anti-tumor activity. Irreversibly binds to the DNA topoisomerase I complex, inhibits DNA recombination after cleavage by topoisomerase I, and locks the enzyme and DNA in a covalent bond. Camptothecin was originally isolated from the stem wood of the Camptotheca acuminata tree and was shown to exhibit antileukemic/antitumor activity, and reversibly inhibit Mitochondrial Topo I (nuclear Topo I (topoisomerase I )) by binding to and stabilizing the topoisomerase-DNA covalent complex. Advancing replication forks are believed to interact with these complexes leading to double strand breaks, which is thought to be responsible for much of the cytotoxicity; other research has shown that some of the antitumor activity could be derived from the inhibition of NOS2 (iNOS or inducible nitric oxide synthase) which generates nitric oxide, an important regulator of angiogenesis and other biochemical pathways. The discovery of camptothecin spurred the development of many derivatives with superior activity and solubility, including irinotecan (sc-202186) and topotecan (sc-204919). Although most noted for its anticancer activity camptothecin and derivatives have shown other pertinent biochemical actions, including: antiprotozoal, antimalarial, inhibition of HIV, upregulation of p53, and induction of apoptosis. This product also exhibits intense blue fluorescence when exposed to UV light, which could be useful in optical experiments. |
| production method | This product is an alkaloid extracted from the root, bark and fruit of Camptotheca species of Davidia involucrata. It can also be produced synthetically. The Camptotheca acuminata fruit meal was immersed in 10-fold amount of 80% ethanol for 24 hours, and the percolation liquid was collected, concentrated under reduced pressure, and the ethanol was recovered. The concentrated liquid was left to stand and the clear liquid was extracted with chloroform, and the extracted liquid was distilled to recover chloroform to dryness, followed by methanol solution, cooling and filtering. The filter cake was crude camptothecin, and the crude product was recrystallized with methanol-chloroform mixed solvent, camptothecin. To crude drug Camptotheca acuminata juice, the total yield was 0.03-0.04%. |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 153 mg/kg; Oral-mouse LD50: 50.1 mg/kg |
| stimulation data | Skin-mouse 0.3% week mild |
| flammability hazard characteristics | thermal decomposition of toxic NOx fumes; Reaction with acid decomposition |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from food raw materials |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
Last Update：2024-04-09 20:13:35
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