Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01199)
Name
Latanoprost
Synonyms    Click to Show/Hide the Synonyms of This API
latanoprost; 130209-82-4; Xalatan; PhXA41; PHXA-41; PhXA 41; XA41; UNII-6Z5B6HVF6O; Latanoprost, ethanol solution; Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate; propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; 6Z5B6HVF6O; CHEBI:6384; propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate; MFCD00216074; XA-41; T-2345; isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprost-5-en-1-oate; Catioprost; (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptanoic acid 1-methylethyl ester; 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, 1-methylethyl ester, (5Z)-; SMR000466354; Xalatan (TN); latanoprost (isopropyl ester); latanoprostum; Nova-21027; Latanoprost [USAN:INN:BAN]; XA 41; PhXA34 [as 15(R,S)-isomer]; propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; AR-202; L-PPDS; Latanoprost, (+/-)-; CHEMBL1051; SCHEMBL24698; MLS000759468; MLS001424106; Latanoprost (JAN/USP/INN); GTPL1961; DTXSID1041057; HMS2051H11; HMS2089J17; HMS3715N22; AMY30089; EX-A1770; HY-B0577; ABP001061; BDBM50240648; s4709; ZINC12468792; Latanoprost, >=98% (HPLC), oil; AKOS024458331; AT-3016; CCG-100946; DB00654; NC00196; NCGC00246969-01; NCGC00246969-06; AS-75099; Isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate; L0262; D00356; 33537-EP2295409A1; 33537-EP2311820A1; AB00640005-04; AB00640005-06; 209L824; A806039; Q634959; SR-01000759428; J-005764; SR-01000759428-4; UNII-8S5FB3XXG8 component GGXICVAJURFBLW-CEYXHVGTSA-N; Latanoprost, United States Pharmacopeia (USP) Reference Standard; Tris(2,4-dimethylphenyl)phosphine-5,5',5''''-trisulfonic acid trisodium salt; (1R,2R,3R,5S,3''R)-7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)-cyclopentyl]-hept-5-enoic acid isopropyl ester; (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid propan-2-yl ester; (Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate; 155551-81-8; 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester; 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1-alpha(Z),2-beta(R*),3-alpha,5-alpha))-; Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-bis(oxidanyl)-2-[(3R)-3-oxidanyl-5-phenyl-pentyl]cyclopentyl]hept-5-enoate
Clinical Status
Approved
PubChem CID
5311221
Formula
C26H40O5
Canonical SMILES
CC(C)OC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
InChI
1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1
InChIKey
GGXICVAJURFBLW-CEYXHVGTSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 432.6 Topological Polar Surface Area 87
XlogP 4.3 Complexity 526
Heavy Atom Count 31 Rotatable Bond Count 14
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Latanoprost 0.005% solution Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Castor Oil; Sodium Borate; Boric Acid; Propylene Glycol; Edetate Disodium; Polyoxyl 15 Hydroxystearate; Sodium Hydroxide; Hydrochloric Acid; Water
                   Dosage Form Solution
                   Company Sun Pharmaceutical Industries
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Ricinoleic acid DIG Info Free fatty acid receptor 4 (EC50 = 1318.26 nM) [1]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
Polyoxyl 15 hydroxystearate DIG Info Albendazole monooxygenase (EC50 = 88.3 uM) [4]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium Chloride; Sodium Dihydrogen Phosphate Monohydrate; Disodium Hydrogen Phosphate Anhydrous; Water
                   Dosage Form Solution
                   Company Greenstone ; Nucare Pharmaceuticals
References
1 Succinct synthesis of saturated hydroxy fatty acids and in vitro evaluation of all hydroxylauric acids on FFA1, FFA4 and GPR84. Med Chem Comm. 2017; 8:1360-1365.
2 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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