Bimatoprost

Iupac Name：(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide

CAS No.: 155206-00-1

Molecular Weight：415.574

Modify Date.: 2022-11-06 11:32

Introduction: Antiglaucoma. Synthetic prostamide; structurally related to prostaglandin F2a. View more+

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1. Names and Identifiers

1.1 Name: Bimatoprost
1.2 Synonyms: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide 17-Phenyltrinor-PGF2α ethylamide 5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)- 5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-N-ethyl-, (5Z)- 5-Heptenamide, 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl]-N-ethyl-, [1R-[1α(Z),2β(1E,3S*),3α,5α]]- 5-Heptenamide,7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)- AGN 192024 Latisse Lumigan Prostamide

1.3 CAS No.: 155206-00-1

1.4 CID: 5311027

1.5 EINECS(EC#): 2017-001-1

1.6 Molecular Formula: C25H37NO4 (isomer)

1.7 Inchi: InChI=1S/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

1.8 InChkey: AQOKCDNYWBIDND-FTOWTWDKSA-N

1.9 Canonical Smiles: CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O

1.10 Isomers Smiles: CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O

2. Properties

2.1 Density: 1.145

2.1 Melting point: 66-68°C

2.1 Boiling point: 629.8 oC at 760 mmHg

2.1 Refractive index: 1.591

2.1 Flash Point: 334.7 oC

2.1 Precise Quality: 415.27200

2.1 PSA: 89.79000

2.1 logP: 3.53780

2.1 Appearance: crystalline solid

2.2 Storage: ?20°C

2.3 Chemical Properties: Crystalline Solid

2.4 Physical: Solid

2.5 pKa: 14.25±0.20(Predicted)

2.6 Water Solubility: very soluble in ethyl alcohol and methyl alcohol and slightly soluble in water.

2.7 StorageTemp: ?20°C

3. Use and Manufacturing

3.1 General Description: Bimatoprost (Lumigan) is supplied as a sterile 0.03%ophthalmic solution in 2.5- and 5.0-mL sizes. The recommendeddosage of bimatoprost is limited to one drop intothe affected eye once daily in the evening. Increased usagemay decrease its beneficial effect. If used concurrently withother IOP-lowering drugs, a waiting period of 5 minutesshould separate administrations. BimatoprostSupplier

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 12 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (16.67%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (41.67%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H319 (75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H340 (50%): May cause genetic defects [Danger Germ cell mutagenicity]
H360 (66.67%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (25%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P322, P330, P337+P313, P363, P405, and P501

3.3 Usage: Antiglaucoma. Synthetic prostamide; structurally related to prostaglandin F2a.

4. Safety and Handling

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Dermal, Category 4

Eye irritation, Category 2

Germ cell mutagenicity, Category 1B

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H312 Harmful in contact with skin H319 Causes serious eye irritation H340 May cause genetic defects H360 May damage fertility or the unborn child
Precautionary statement(s)
Prevention	P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

155206-00-1Total: 35 Synthesis Route

4509-90-4 91 Suppliers

155206-00-1 310 Suppliers

Literatures:
WO2013/186550 A1, ;
Yield: null

2067-33-6 154 Suppliers

155206-00-1 310 Suppliers

Literatures:
WO2013/186550 A1, ;
Yield: null

64091-14-1 3 Suppliers

155206-00-1 310 Suppliers

Literatures:
US2012/16136 A1, ;
Yield: null

View all

7. Precursor and Product

precursor:

98974-31-3

1415393-93-9

64091-14-1

2067-33-6

1513876-42-0

1300092-89-0

1300092-91-4

4509-90-4

1300092-92-5

179011-80-4

38344-08-0

329313-36-2

1355995-17-3

1300093-14-4

1240483-18-4

41639-73-0

1240483-19-5

17814-85-6

1240483-16-2

41162-19-0

856240-62-5

1240483-17-3

1240483-14-0

1240483-15-1

View all

8. Other Information

8.0 Side effects: 1. to deepen the color of the iris, blepharitis, eye irritation and pain; black eyelashes thicker growth; conjunctival hyperemia, temporarily punctate corneal epithelial erosion, eyelid edema and erythema; rash.
2. rare respiratory disorders, asthma exacerbations, iritis, uveitis, eyelid skin darkening.
3. very rare chest pain, pharyngitis.
4. eye itching, allergic conjunctivitis, cataract, conjunctival edema, secretions, photophobia, superficial punctate keratitis, headache, high blood pressure.

8.1 Chemical Properties: Crystalline Solid

8.2 Uses: Antiglaucoma. Synthetic prostamide; structurally related to prostaglandin F2a.

8.3 Uses: Bimatoprost is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes. It ha

8.4 Uses: Bimatoprost is an antiglaucoma agent. Bimatoprost is an synthetic prostamide; structurally related to prostaglandin F2α.

8.5 Brand name: Lumigan (Allergan).

9. Computational chemical data

Molecular Weight: 415.574g/mol
Molecular Formula: C₂₅H₃₇NO₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 415.27225866
Monoisotopic Mass: 415.27225866
Complexity: 541
Rotatable Bond Count: 12
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 89.8
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 2
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB6OAAAAAAAAAAAAAAAAAAAAYAAAAAwAAAAAAAAAAABAAAAHgAQCAAADRThmAYyAILAAgCIAiFSEAACAAAgAAAIiIEIAIgINDKAkRCEcAAl1gCImAfYwKAOgAAAAAAAAAAAAAAAAAAAAIQADAAAAA==

10. Question & Answer

The uses and side effects of Bimatoprost Apr 27 2021
Description Bimatoprost, also known as Latisse or Lumigan, belongs to a group of drugs called prostamides, which are synthetic structural analogs of prostaglandin. Bimatoprost, marketed by Allergan, is administered in an ophthalmic solution and has the ability to reduce ocular hypotension, proving ...

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