Hydroxyprogesterone caproate

Details

• Internal ID: 6f3ff29e-e0ef-48ad-8a6e-3d244068ffe8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
• SMILES (Canonical): CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
• SMILES (Isomeric): CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)C(=O)C
• InChI: InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
• InChI Key: DOMWKUIIPQCAJU-LJHIYBGHSA-N
• Popularity: 536 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₄
• Molecular Weight: 428.60 g/mol
• Exact Mass: 428.29265975 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.97
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 630-56-8
• Delalutin
• Primolut Depot
• Hydroxyprogesterone hexanoate
• Hormofort
• Proge
• Syngynon
• Depo-Proluton
• Proluton Depot
• Hylutin
• Teralutil
• Makena
• Estralutin
• Hyproval
• Kaprogest
• Lutate
• Relutin
• Progesterone caproate
• Neolutin forte
• 17-Caproxyprogesterone
• Idrogestene
• Duraluton
• Hyroxon
• Luteocrin
• Lutopron
• Luteocrin depot
• Hyproval-PA
• 17alpha-Hydroxyprogesterone caproate
• NSC-17592
• 17-alpha-hydroxy-progesterone caproate
• Corlutin L.A.
• Gesterol LA 250
• 17-OHPC
• Gestiva
• Procyte depo
• Progesterone retard pharlon
• 17alpha-Caproyloxypregn-4-ene-3,20-dione
• Delalutin (TN)
• 17-alpha-Hydroxyprogesterone caproate
• 17-((1-Oxohexyl)oxy)pregn-4-ene-3,20-dione
• MLS000028438
• 17a-hydroxyprogesterone caproate
• Oxiprogesterone Caproate
• Idroprogesterone caproato
• 17 alpha-hydroxyprogesterone caproate
• 17alpha-Hydroxyprogesterone hexanoate
• Hydroxyprogesteroni caproas
• 17.alpha.-caproyloxy-p4
• Progesterone, 17-hydroxy-, hexanoate
• Caproate d'hydroxyprogesterone
• SMR000058336
• Caproato de hidroxiprogesterona
• MLS001148643
• CHEBI:5812
• DTXSID6043915
• UNII-276F2O42F5
• 17-Hydroxypregn-4-ene-3,20-dione hexanoate
• 17a-Hydroxyprogesterone hexanoate
• Idroprogesterone caproato [DCIT]
• EINECS 211-138-8
• Pregn-4-ene-3,20-dione, 17-hydroxy-, hexanoate
• Pregn-4-ene-3,20-dione, 17-((1-oxohexyl)oxy)-
• 17-alpha-Hydroxyprogesterone hexanoate
• 17.alpha.-Hydroxyprogesterone caproate
• 17alpha-Hydroxyprogesterone n-caproate
• 276F2O42F5
• (8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl hexanoate
• 17.alpha.-Hydroxyprogesterone hexanoate
• Hydroxyprogesteroni caproas [INN-Latin]
• oxyprogesterone caproate
• NCGC00021268-03
• 17-alpha-Hydroxy progesterone n-caproate
• 17.alpha.-Hydroxyprogesterone n-caproate
• 3,20-Dioxo-4-pregnen-17alpha-yl hexanoat
• 3,20-Dioxopregn-4-en-17alpha-yl caproate
• Caproate d'hydroxyprogesterone [INN-French]
• Hydroxyprogesterone caproate [USP:INN:JAN]
• 17alpha-Hydroxyprogesterone-17alpha caproate
• 17-alpha-Hexanoyloxypregn-4-ene-3,20-dione
• Caproato de hidroxiprogesterona [INN-Spanish]
• 3,20-Dioxopregn-4-en-17.alpha.-yl caproate
• 17.alpha.-Hydroxypregn-4-ene-3,20-dione hexanoate
• Pregn-4-ene-3,20-dione, 17-[(1-oxohexyl)oxy]-
• DTXCID4023915
• Hexanoic acid, ester with 17-hydroxypregn-4-ene-3,20-dione
• CAS-630-56-8
• 17|A-Hydroxyprogesterone caproate
• [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
• Lewntogest
• 17|A-Hydroxyprogesterone hexanoate
• Hyproval P.A.
• Hylutin (TN)
• Makena (TN)
• Hydroxyprogesterone caproate [USAN:INN:JAN]
• Proluton depot (TN)
• Progesterone, hexanoate
• 17alpha-Hydroxyprogesterone caproate [Progestins]
• 17-Caproyloxyprogesterone
• Opera_ID_1479
• D00AEQ
• Deluteval 2X (Salt/Mix)
• SCHEMBL5330
• MLS002207289
• 17alpha-Caproyloxyprogesterone
• 17-hydroxyprogesterone-caproate
• Caproic acid hydroxyprogesterone
• cid_169870
• CHEMBL1200848
• BDBM70293
• 17alpha-Hydroxyprogesteron-Caproat
• HMS2230L08
• BCP16081
• HY-B0742
• NSC17592
• Tox21_113502
• Tox21_302333
• 17-alpha hydroxyprogesterone caproate
• MFCD00072134
• s4674
• AKOS005267159
• Tox21_113502_1
• 17 alpha -Hydroxyprogesterone Caproate
• CCG-268987
• DB06789
• GS-3233
• NCGC00021268-04
• NCGC00255784-01
• (1S,11S,15S,2R,10R,14R)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0<2,7>.0 <11,15>]heptadec-6-en-14-yl hexanoate
• HYDROXYPROGESTERONE CAPROATE [INN]
• HYDROXYPROGESTERONE CAPROATE [JAN]
• Pregn-4-ene-3, 17-hydroxy-, hexanoate
• 17alpha-hexanoyloxy-4pregnene-3,20-dione
• Hydroxyprogesterone caproate (JAN/USP/INN)
• HYDROXYPROGESTERONE CAPROATE [MART.]
• HYDROXYPROGESTERONE CAPROATE [VANDF]
• Pregn-4-ene-3, 17-[(1-oxohexyl)oxy]-
• 17-Hydroxypregn-4-ene-3,20-dione caproate
• H0994
• HYDROXYPROGESTERONE CAPROATE [USP-RS]
• HYDROXYPROGESTERONE CAPROATE [WHO-DD]
• 17alpha-Hydroxyprogesterone hexanoate, >=98%
• C08148
• D00949
• H10189
• 17-.alpha.-Hexanoyloxypregn-4-ene-3,20-dione
• 17alpha-Hydroxypregn-4-ene-3,20-diene Caproate
• EN300-7422372
• 3,20-Dioxopregn-4-en-17.alpha.-yl hexanoate #
• A834188
• HYDROXYPROGESTERONE CAPROATE [ORANGE BOOK]
• SR-01000003075
• 17.alpha.-Hydroxypregn-4-ene-3,20-dione caproate
• 17.ALPHA.-HYDROXYPROGESTERONE CAPROATE [MI]
• HYDROXYPROGESTERONE CAPROATE [USP MONOGRAPH]
• Q-201222
• Q3792032
• SR-01000003075-3
• 17-Hydroxyprogesterone hexanoate;17-Hydroxyprogesterone caproate
• Hydroxyprogesterone caproate, United States Pharmacopeia (USP) Reference Standard
• (1R,3aS,3bR,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl hexanoate
• (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl hexanoate
• [(10R,13S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
• [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate;17-Caproxyprogesterone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.6779	67.79%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7363	73.63%
OATP2B1 inhibitior	-	0.8740	87.40%
OATP1B1 inhibitior	-	0.7738	77.38%
OATP1B3 inhibitior	+	0.9636	96.36%
MATE1 inhibitior	+	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9607	96.07%
P-glycoprotein inhibitior	+	0.8899	88.99%
P-glycoprotein substrate	-	0.6795	67.95%
CYP3A4 substrate	+	0.7356	73.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9075	90.75%
CYP3A4 inhibition	-	0.6829	68.29%
CYP2C9 inhibition	-	0.8914	89.14%
CYP2C19 inhibition	-	0.7800	78.00%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.9505	95.05%
CYP2C8 inhibition	+	0.7092	70.92%
CYP inhibitory promiscuity	-	0.7134	71.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5940	59.40%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9544	95.44%
Skin irritation	+	0.6200	62.00%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8548	85.48%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6260	62.60%
skin sensitisation	-	0.8087	80.87%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8001	80.01%
Acute Oral Toxicity (c)	IV	0.6445	64.45%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.9092	90.92%
Thyroid receptor binding	+	0.5396	53.96%
Glucocorticoid receptor binding	+	0.9143	91.43%
Aromatase binding	+	0.7682	76.82%
PPAR gamma	+	0.5229	52.29%
Honey bee toxicity	-	0.8811	88.11%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6718	67.18%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	10000 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	19952.6 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	19952.6 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.24%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.98%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.24%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.36%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.04%	98.95%
CHEMBL1871	P10275	Androgen Receptor	92.06%	96.43%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.64%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.57%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.46%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	90.71%	90.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.36%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	88.61%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.95%	86.33%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.11%	89.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.79%	95.56%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.48%	94.78%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.05%	92.86%
CHEMBL340	P08684	Cytochrome P450 3A4	83.07%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.88%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.86%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.45%	94.33%
CHEMBL299	P17252	Protein kinase C alpha	81.97%	98.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.27%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.04%	92.62%
CHEMBL255	P29275	Adenosine A2b receptor	81.03%	98.59%
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	80.18%	86.00%

Plants that contains it

• Chaenomeles sinensis
• Trivalvaria costata

Cross-Links

• PubChem: 169870
• NPASS: NPC305039
• ChEMBL: CHEMBL1200848