Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00828)
Name
Alprostadil
Synonyms    Click to Show/Hide the Synonyms of This API
alprostadil; Prostaglandin E1; 745-65-3; PGE1; Edex; Caverject; Muse; Prostin VR; Alprostadilum; Femprox; Befar; Alprox-TD; l-Prostaglandin E1; Liprostin; Prostandin; Vitaros; PGE-1; Topiglan; Alprostadil(Caverject); (11alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid; MR-256; UNII-F5TD010360; (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate; 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid; 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoic acid; CHEMBL495; Vasaprostan; CHEBI:15544; 9-oxo-11R,15S-dihydroxy-13E-prostaenoic acid; U-10136; 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid; F5TD010360; Minprog; Sugiran; Viridal; (13E,15S)-11alpha,15-dihydroxy-9-oxoprost-13-en-1-oic acid; PGE1 Oligomer; U-10,136; Prostin VR Pediatric; Lipoprost; Promostan; Prostivas; Alista; Prink; FemLife; ProstaglandinE1; RayVa; Caverject Impulse; PGE1alpha; 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)heptanoic acid; 7-[(1r,3r)-3-Hydroxy-2-[(1e,3s)-3-Hydroxyoct-1-En-1-Yl]-5-Oxocyclopentyl]heptanoic Acid; SMR000112594; (-)-Prostaglandin E1; Befar (TN); Prink (TN); Edex (TN); Muse (TN); (-)-Protaglandin E1; U 10136; l-PGE1; SR-01000597593; MR 256; Alprostadilum [INN-Latin]; Prostin VR pediatric (TN); Alprostadil Prostoglandin E1; BML1-F06; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid; Alprostadil(usan); NSC-165559; HEI-507; NCGC00016535-01; 119314-69-1; CAS-745-65-3; ONO 1608; EINECS 212-017-2; (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate; NSC 165559; Alprostadil [USAN:USP:INN:BAN:JAN]; 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid; PGE1;Prostaglandin E1; AI3-62116; Prestwick2_001018; Prestwick3_001018; DSSTox_CID_2578; Prostaglandin E1, 98+%; DSSTox_RID_76640; DSSTox_GSID_22578; SCHEMBL33317; BSPBio_001175; BSPBio_001488; MLS000758964; MLS001424250; BIDD:GT0747; BPBio1_001293; GTPL1882; Alprostadil (JP17/USP/INN); DTXSID9022578; PGE1, Prostaglandin E1, powder; SYN3025; HMS1361K10; HMS1571K17; HMS1791K10; HMS1989K10; HMS2052L11; HMS2090L08; HMS2098K17; HMS3268I09; HMS3402K10; HMS3414N09; HMS3648O17; HMS3678N07; HMS3715K17; (11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid; AMY30076; BCP01740; EX-A1411; HY-B0131; ONO-1608; ZINC3813088; Tox21_110482; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid; BDBM50101853; l-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid; LMFA03010134; MFCD00077860; s1508; AKOS015961103; Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11.alpha.,13E,15S)-; Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11alpha,13E,15S)-; AC-6095; BCP9000277; CCG-101188; CS-1905; DB00770; NC00438; (1R,2R,3R)-3-Hydroxy-2-((E)-(3S)-3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid; IDI1_033958; Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11alpha,13E,15S)-, homopolymer; Prostaglandin E1, >=99.0% (TLC); SMP2_000271; NCGC00025234-02; NCGC00025234-03; NCGC00025234-04; NCGC00025234-05; AS-16360; K274; AB0014134; 11,15-Dihydroxy-9-oxoprost-13-en-1-oate; AB00514004; B2154; ST50826271; Alprostadil, meets USP testing specifications; A11820; C04741; D00180; Prostaglandin E1, >=98% (HPLC), synthetic; AB00514004-06; AB00514004-08; AB00514004_09; 745P653; Q579348; SR-01000946253; SR-01000597593-1; SR-01000597593-5; SR-01000597593-6; SR-01000946253-1; W-104416; BRD-K52459643-001-06-0; BRD-K52459643-001-10-2; BRD-K52459643-001-17-7; (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoate; (13E)-(15S)-11,15-dihydroxy-9-oxoprost-13-enoic acid; Alprostadil, European Pharmacopoeia (EP) Reference Standard; (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoic acid; (11?,13E,15S)-11,15-Dihydroxy-9-oxo-prost-13-en-1-oic acid; (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoic acid; 11,15-dihydroxy-9-oxoprost-13-en-1-oic acid (ACD/Name 4.0); 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate; Alprostadil, United States Pharmacopeia (USP) Reference Standard; (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate; (+)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid; (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoate; (-)-3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-Cyclopentaneheptanoic acid; (11alpha,12alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid; Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, l-; Prostaglandin E1, synthetic, powder, BioReagent, suitable for cell culture; Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)-; Prostaglandin E1, powder, gamma-irradiated, BioXtra, suitable for cell culture; 7-[5-((1E)(3S)-3-hydroxyoct-1-enyl)(1R,4R,5R)-4-hydroxy-2-oxocyclopentyl]hepta noic acid; XPG
Clinical Status
Approved
PubChem CID
5280723
Formula
C20H34O5
Canonical SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
InChI
1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChIKey
GMVPRGQOIOIIMI-DWKJAMRDSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5280723"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 354.5 Topological Polar Surface Area 94.8
XlogP 3.2 Complexity 432
Heavy Atom Count 25 Rotatable Bond Count 13
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Alprostadil 0.01mg/vial injectable Click to Show/Hide the Full List of Formulation(s):          1 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
Alpha Cyclodextrin; Lactose; Sodium Citrate; Benzyl Alcohol; Hydrochloric Acid; Sodium Hydroxide
                   Dosage Form Injectable
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [1]
Alfadex DIG Info Norepinephrine transporter (Ki = 1260 nM) [2]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [3]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [4]
          Alprostadil 0.005mg/vial injectable Click to Show/Hide the Full List of Formulation(s):          1 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
Sodium Chloride; -Cyclodextrin; Lactose
                   Dosage Form Injectable
                   Company Auxilium Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Alfadex DIG Info Norepinephrine transporter (Ki = 1260 nM) [2]
References
1 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
2 DrugMatrix in vitro pharmacology data.
3 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
4 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.

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