Alprostadil

Details

• Internal ID: 12f5aae0-85eb-4745-b0ab-ab3db2b8c8c3
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)O)O)O
• InChI: 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
• InChI Key: GMVPRGQOIOIIMI-DWKJAMRDSA-N
• Popularity: 9,985 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.50 g/mol
• Exact Mass: 354.24062418 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.48
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 13

Synonyms

• Prostaglandin E1
• 745-65-3
• PGE1
• Edex
• Caverject
• Muse
• Prostin VR
• Prostavasin
• Befar
• Alprostadilum
• Femprox
• Topiglan
• Alprox-TD
• Liprostin
• Prostandin
• l-Prostaglandin E1
• Vitaros
• Prink
• Prostin VR Pediatric
• PGE-1
• Lipoprost
• Promostan
• Prostivas
• Caverject Impulse
• PGE1alpha
• (-)-Protaglandin E1
• (11alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid
• l-PGE1
• (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
• U-10136
• DTXSID9022578
• UNII-F5TD010360
• Alprostadil(Caverject)
• CHEBI:15544
• (-)-Prostaglandin E1
• ONO 1608
• ONO-1608
• EINECS 212-017-2
• CHEMBL495
• Alprostadilum [INN-Latin]
• F5TD010360
• NSC 165559
• NSC-165559
• U-10,136
• AI3-62116
• DTXCID502578
• Vasaprostan
• (13E,15S)-11alpha,15-dihydroxy-9-oxoprost-13-en-1-oic acid
• 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
• Alprostadil [USAN:USP:INN:BAN:JAN]
• Minprog
• Sugiran
• Viridal
• 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
• l-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
• Alprostadilum (INN-Latin)
• Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11alpha,13E,15S)-
• (1R,2R,3R)-3-Hydroxy-2-((E)-(3S)-3-hydroxy-1-octenyl)-5-oxocyclopentaneheptanoic acid
• ALPROSTADIL (MART.)
• ALPROSTADIL [MART.]
• ALPROSTADIL (USP-RS)
• ALPROSTADIL [USP-RS]
• (13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate
• ALPROSTADIL (USP IMPURITY)
• ALPROSTADIL [USP IMPURITY]
• Alista
• ALPROSTADIL (USP MONOGRAPH)
• ALPROSTADIL [USP MONOGRAPH]
• FemLife
• ProstaglandinE1
• RayVa
• Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, (-)-
• Cyclopentaneheptanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, l-
• Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11a,13E,15S)-
• 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
• Alprostadil (USAN:USP:INN:BAN:JAN)
• SMR000112594
• Lipo-PGE1
• Befar (TN)
• Prink (TN)
• Prostaglandin E1alpha
• Edex (TN)
• Muse (TN)
• SR-01000597593
• MR-256
• Prostin VR pediatric (TN)
• Alprostadil Prostoglandin E1
• BML1-F06
• NSC165559
• Alprostadil(usan)
• (1R,2R,3R)-3-Hydroxy-2-[(E)-(3S)-3-hydroxy-1-octenyl]-5-oxocyclopentaneheptanoic acid
• HEI-507
• NCGC00016535-01
• 7-((1R,2R,3R)-3-Hydroxy-2-((1E,3S)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoic acid
• 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
• Alprostadil; 7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
• CAS-745-65-3
• MFCD00077860
• 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid
• PGE1;Prostaglandin E1
• Prestwick2_001018
• Prestwick3_001018
• ALPROSTADIL [INN]
• ALPROSTADIL [JAN]
• PROSTINVR PEDIATRIC
• ALPROSTADIL [USAN]
• ALPROSTADIL [VANDF]
• PGE1 (Prostaglandin E1)
• SCHEMBL33317
• ALPROSTADIL [WHO-DD]
• BSPBio_001175
• BSPBio_001488
• MLS000758964
• MLS001424250
• BIDD:GT0747
• PROSTAGLANDIN E1 [MI]
• BPBio1_001293
• GTPL1882
• Alprostadil (JP17/USP/INN)
• ALPROSTADIL [ORANGE BOOK]
• C01EA01
• G04BE01
• PGE1, Prostaglandin E1, powder
• HMS1361K10
• HMS1571K17
• HMS1791K10
• HMS1989K10
• HMS2052L11
• HMS2090L08
• HMS2098K17
• HMS3268I09
• HMS3402K10
• HMS3414N09
• HMS3648O17
• HMS3678N07
• HMS3715K17
• AMY30076
• BCP01740
• EX-A1411
• HY-B0131
• Tox21_110482
• 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid
• BDBM50101853
• LMFA03010134
• s1508
• AKOS015961103
• Prost-13-en-1-oic acid, 11,15-dihydroxy-9-oxo-, (11.alpha.,13E,15S)-
• AC-6095
• BCP9000277
• CCG-101188
• CS-1905
• DB00770
• NC00438
• IDI1_033958
• Prostaglandin E1, >=99.0% (TLC)
• SMP2_000271
• NCGC00025234-02
• NCGC00025234-03
• NCGC00025234-04
• NCGC00025234-05
• AS-16360
• Prostaglandin E1, PGE1, 745-65-3
• Alprostadil 100 microg/mL in Acetonitrile
• Muse (intraurethral alprostadil suppository)
• 11,15-Dihydroxy-9-oxoprost-13-en-1-oate
• AB00514004
• P1917
• Alprostadil, meets USP testing specifications
• C04741
• C76381
• D00180
• Prostaglandin E1, >=98% (HPLC), synthetic
• AB00514004-06
• AB00514004-08
• AB00514004_09
• 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acidl
• A838163
• EN300-22411483
• 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
• Prostaglandin E1, synthetic, powder, BioReagent, suitable for cell culture
• Prostaglandin E1, powder, gamma-irradiated, BioXtra, suitable for cell culture
• XPG

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	-	0.8075	80.75%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Mitochondria	0.8162	81.62%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7351	73.51%
P-glycoprotein inhibitior	-	0.8050	80.50%
P-glycoprotein substrate	-	0.6295	62.95%
CYP3A4 substrate	+	0.5696	56.96%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9502	95.02%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8814	88.14%
CYP inhibitory promiscuity	-	0.9725	97.25%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7224	72.24%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.5568	55.68%
Skin corrosion	-	0.8674	86.74%
Ames mutagenesis	-	0.8778	87.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5281	52.81%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.6351	63.51%
skin sensitisation	-	0.8636	86.36%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7592	75.92%
Acute Oral Toxicity (c)	III	0.6983	69.83%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.7156	71.56%
Thyroid receptor binding	+	0.5146	51.46%
Glucocorticoid receptor binding	+	0.7511	75.11%
Aromatase binding	-	0.7513	75.13%
PPAR gamma	+	0.5601	56.01%
Honey bee toxicity	-	0.9457	94.57%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5665	56.65%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10 nM	Potency	via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	20 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	6.3 nM	Potency	via Super-PRED
CHEMBL1881	P43116	Prostanoid EP2 receptor	16.5 nM	EC50	via Super-PRED
CHEMBL1836	P35408	Prostanoid EP4 receptor	0.22 nM	EC50	via Super-PRED
CHEMBL1995	P43119	Prostanoid IP receptor	150 nM	Ki	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	2.5 nM; 10 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.09%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.62%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.39%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	94.56%	89.63%
CHEMBL299	P17252	Protein kinase C alpha	94.12%	98.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.77%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.39%	92.08%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	88.42%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.27%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.87%	90.71%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	87.22%	92.26%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.84%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	86.42%	97.79%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.66%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.53%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.39%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	83.67%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	83.50%	94.73%
CHEMBL1902	P62942	FK506-binding protein 1A	83.45%	97.05%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.44%	97.29%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.88%	91.81%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.96%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.71%	89.00%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	80.04%	98.00%

Plants that contains it

• Larix sibirica
• Lindera erythrocarpa
• Populus balsamifera

Cross-Links

• PubChem: 5280723
• LOTUS: LTS0091084
• wikiData: Q105149696