(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Names and Identifiers

Name	Bimatoprost
Synonyms	LUMIGAN BIMATOPROST Bimatoprost Bimatoprost(TM) BIMATOPROST(TM) BIMATOPROST(LUMIGAN) Bimatoprost(LUMIGAN) 17-phenyl-tri-norprostaglandin f2α-ethyl amide 17-phenyl TRINOR prostaglandin F2ALPHA ethyl amide 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ETHYL AMIDE N-ETHYL-9ALPHA,11ALPHA,15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROSTA-5Z, 13E-DIEN-1-AMIDE N-ethyl-9ALPHA,11ALPHA,15S-Trihydroxy-17-phenyl-18,19,20-TRINOR-PROSTA-5Z, 13E-DIEN-1-amide (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide (5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide
CAS	155206-00-1
EINECS	642-890-9
InChI	InChI=1/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3+,17-16+/t20-,21+,22+,23-,24+/m0/s1
InChIKey	AQOKCDNYWBIDND-FTOWTWDKSA-N

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Physico-chemical Properties

Molecular Formula	C25H37NO4
Molar Mass	415.57
Density	1.145±0.06 g/cm3(Predicted)
Melting Point	66-68°C
Boling Point	629.8±55.0 °C(Predicted)
Flash Point	334.7°C
Solubility	Soluble in ethanol (~50 mg/ml), methanol, DMSO (~25 mg/ml), DMF (~25 mg/ml), and PBS (
Vapor Presure	9.94E-17mmHg at 25°C
Appearance	Crystalline solid
Color	White to Off-White
pKa	14.25±0.20(Predicted)
Storage Condition	-20°C
Stability	Light Sensitive
Refractive Index	1.591

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Risk and Safety

WGK Germany

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Reference

Reference

1. Pan Chen, Xu Yong, Han Jing, et al. Determination of bimatoprost in eyelash growth liquid cosmetics by high performance liquid chromatography-tandem mass spectrometry [J]. Journal of Analytical Testing, 2020(7).

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Nature

Open Data Verified Data

crystalline powder. Soluble in ethanol and methanol, slightly soluble in water.

Last Update：2024-01-02 23:10:35

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Preparation Method

Open Data Verified Data

with (3aR,4R,5R,6as)-hexahydro-4-(3-oxygen -5-phenyl-1E-pentenyl) -5-(p-phenyl butyryloxy)-2H-cyclopento [B] furan -2-ketone as raw material. After reduction, the carbonyl group on the furan ring is reduced to a hydroxyl group, which is hydrolyzed and then condensed with triphenylphosphine of valeric acid to obtain 7-[(1R,2R,3R,5S)-3,5-= hydroxy 2 A [(3 S) a 5 phenyl -3-[(tetrahydro-2-H-pyran-2-yl) oxy]-1E-pentenyl] cyclopentyl]-52-heptenoic acid. Hydrolysis removes the protecting group on the hydroxyl group of the pentenyl side chain. Methyl Ester was obtained by dissolving methyl iodide in dimethylformamide under the action of Cs2 C03, and finally reacted with an aqueous solution of ethylamine to obtain the product.

Last Update：2022-01-01 09:23:52

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Use

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developed by Allergan, Inc., USA, was first launched in the United States in 2001. Prostaglandin F2 a stimulator. The product selectively mimics the action of prostacyclin produced in the body, lowering intraocular pressure by increasing aqueous humor flow in the scleral pathway of the microscleral network and the pigmented layer. It is used in patients with open-angle glaucoma, or in patients with elevated intraocular pressure who are ineffective with other intraocular pressure lowering drugs (cannot reach a predetermined level of intraocular pressure after multiple measurements) or cannot tolerate.

Last Update：2022-01-01 09:23:53

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide

Bimatoprost

CAS: 155206-00-1

Molecular Formula: C25H37NO4

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Names and Identifiers

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Physico-chemical Properties

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Risk and Safety

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Reference

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Nature

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Preparation Method

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Use

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide Request for Quotation

Bimatoprost

CAS: 155206-00-1

Molecular Formula: C25H37NO4

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Names and Identifiers

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Physico-chemical Properties

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Risk and Safety

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Reference

(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Nature

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Preparation Method

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide - Use

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(5E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl}-N-ethylhept-5-enamide