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Bimatoprost
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  • Name Bimatoprost
  • EINECS642-890-9
  • CAS No. 155206-00-1
  • Density1.145 g/cm3
  • PSA89.79000
  • LogP3.53780
  • Solubilityvery soluble in ethyl alcohol and methyl alcohol and slightly soluble in water
  • Melting Point66-68°C
  • FormulaC25H37NO4
  • Boiling Point629.8 ºC at 760 mmHg
  • Molecular Weight415.573
  • Flash Point334.7 ºC
  • Transport InformationN/A
  • Appearancecrystalline solid
  • Safety
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 155206-00-1 (Bimatoprost)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data34

Bimatoprost Synthetic route

1240483-19-5

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide

155206-00-1

bimatoprost

Conditions
ConditionsYield
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h;
Stage #2: In tetrahydrofuran pH=6.8; Aqueous phosphate buffer;		91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18h;
Stage #2: In tetrahydrofuran; water pH=6.8; Aqueous phosphate buffer;		91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With ammonium hydrogen difluoride In tetrahydrofuran at 20 - 40℃; for 24h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran; tert-butyl methyl ether Product distribution / selectivity;		80%
With hydrogenchloride; water In methanol at 15 - 20℃;
1430731-70-6

2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
In water at 20℃; for 72h;87.2%
1393740-68-5

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

155206-00-1

bimatoprost

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 22h;86%

2,2-bis(hydroxymethyl)propyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

75-04-7

ethylamine

A

1163135-95-2

(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide

B

155206-00-1

bimatoprost

Conditions
ConditionsYield
In water at 20℃; for 72h; Overall yield = 87.2 %; Overall yield = 8.12 g;A n/a
B 83.7%
In water for 60h;A n/a
B 73%
75-04-7

ethylamine

38315-47-8

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester

155206-00-1

bimatoprost

Conditions
ConditionsYield
In methanol at 24 - 27℃; for 72h; Product distribution / selectivity;80%
In water at 20℃; for 60h;62%
In methanol; water at 90℃; for 45h;
856240-62-5

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol

1201226-16-5

(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide

155206-00-1

bimatoprost

Conditions
ConditionsYield
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;		80%
Stage #1: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h;
Stage #2: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide In tetrahydrofuran at 0℃;		65%
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;
Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;		41%
960056-50-2

(9S,11R,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
With water at 20℃; for 60h;80%
856240-52-3

(5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamide

155206-00-1

bimatoprost

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;77.5%
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;77.5%

C23H30O4

75-04-7

ethylamine

155206-00-1

bimatoprost

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran at 20 - 40℃; for 18h; Product distribution / selectivity;67.3%
107-10-8

propylamine

130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

155206-00-1

bimatoprost

Conditions
ConditionsYield
In methanol at 90℃;62%

Bimatoprost Specification

1. Introduction of Bimatoprost
Bimatoprost is crystalline solid. The Product Categories of this chemical is Prostaglandins; Prostaglandin; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Arachidonic Acid Cascade; Lipids in Cell Signaling. The Classification Code of Bimatoprost is Antiglaucoma agent; Antihypertensive Agents; Cardiovascular Agents; Lowers intraocular pressure [IOP] in patients with open angle glaucoma or ocular hypertension [synthetic prostamide analog]. It should be store at -20 °C. Bimatoprost is very soluble in ethanol and methanol, and slightly soluble in water.

2. Properties of Bimatoprost
Physical properties about Bimatoprost are:
(1)H bond acceptors: 5; (2)H bond donors: 4; (3)Freely Rotating Bonds: 15; (4)Index of Refraction: 1.591; (5)Molar Refractivity: 122.67 cm3; (6)Molar Volume: 362.8 cm3; (7)Surface Tension: 48 dyne/cm; (8)Density: 1.145 g/cm3; (9)Flash Point: 334.7 °C; (10)Enthalpy of Vaporization: 97.93 kJ/mol; (11)Boiling Point: 629.8 °C at 760 mmHg; (12)Vapour Pressure: 9.94E-17 mmHg at 25 °C.

3. Structure Descriptors of Bimatoprost
(1)Canonical SMILES: CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
(2)Isomeric 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
(3)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
(4)InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N

4. Safety Information of Bimatoprost
WGK Germany: 3

5. Uses of Bimatoprost
Bimatoprost (CAS NO.155206-00-1) is used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. As an antiglaucoma, Bimatoprost can be used to synthetic prostamide or structurally related to prostaglandin F2α. Usually, it has been used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It can be used in the cosmetic use. In 2008-2011, at least three case series suggested that bimatoprost has the ability to reduce adipose (fat) tissue.

6. Production of Bimatoprost
(3AR, 4R, 5R, 6AS)-six hydrogen-4-(3-oxygen-5-phenyl-1 e-pentenyl)-5-(p-phenyl butyryl oxygen base)-2 h-ring pentaerythritol and [b] furan-2-ketone can be used to manufacture the Bimatoprost. The detailed steps of it is:
By the reduction reaction, and then to restore the carbonyl group on the furan ring is hydroxy, the hydrolysis before and valeric triphenylphosphine to afford 7-(1R, 2R, 3R, 5S) -3,5-two hydroxy-2 -[(3S) -5-phenyl-3-[(tetrahydro-2-H-pyran-2-yl)-oxygen]-1E-pentenyl] cyclopentyl]-5Z-heptenoic acid. Hydrolysis stripped pentenyl the protecting group on the hydroxyl group of the side chain. Was dissolved in dimethyl formamide and then iodomethane, Cs2CO3 role methyl, and finally reaction with the aqueous solution of ethylamine to get this product.

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