Natural Product (NP) Details

General Information of the NP (ID: NP5035)
Name
Alprostadil
Synonyms
alprostadil; Prostaglandin E1; 745-65-3; PGE1; Edex; Caverject; Muse; Prostin VR; Alprostadilum; Topiglan; Femprox; Befar; Alprox-TD; l-Prostaglandin E1; Liprostin; Prostandin; Vitaros; PGE-1; 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; 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; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic 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; Alprostadil 100 microg/mL in Acetonitrile; 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
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Erectile dysfunction [ICD-11: HA01] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C20H34O5
PubChem CID
5280723
Canonical SMILES
CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=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
CAS Number
CAS 745-65-3
ChEBI ID
CHEBI:15544
TTD Drug ID
D0I4DQ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Trimetazidine      Angina pectoris     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)		 Trimetazidine and plasmin combined with alprostadil can effectively treat lower extremity arteriosclerosis obliterans.
Target and Pathway
Target(s) Prostaglandin E2 receptor EP2 (PTGER2)  Molecule Info  [3]
Thromboxane A2 receptor (TBXA2R)  Molecule Info  [4]
KEGG Pathway cAMP signaling pathway Click to Show/Hide
2 Neuroactive ligand-receptor interaction
3 Inflammatory mediator regulation of TRP channels
4 Renin secretion
5 Pathways in cancer
6 Calcium signaling pathway
7 Platelet activation
Reactome Prostanoid ligand receptors Click to Show/Hide
2 G alpha (s) signalling events
3 G alpha (q) signalling events
4 G alpha (12/13) signalling events
5 Thromboxane signalling through TP receptor
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 Ovarian Infertility Genes
4 Small Ligand GPCRs
5 GPCR ligand binding
6 GPCR downstream signaling
7 Gastrin-CREB signalling pathway via PKC and MAPK
8 Signal amplification
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1882).
Reference 2 Efficacy of trimetazidine and plasmin combined with alprostadil in treatment of lower extremity arteriosclerosis obliterans. Exp Ther Med. 2019 Jun;17(6):4554-4560.
Reference 3 Emerging drugs for diabetic foot ulcers. Expert Opin Emerg Drugs. 2006 Nov;11(4):709-24.
Reference 4 Flow after prostaglandin E1 is mediated by receptor-coupled adenylyl cyclase in human anterior segments. Invest Ophthalmol Vis Sci. 1999 Oct;40(11):2622-6.
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