Identification
NameHydroxyprogesterone caproate
Accession NumberDB06789
TypeSmall Molecule
GroupsApproved
Description

Hydroxyprogesterone caproate is a synthetic steroid hormone that is similar to medroxyprogesterone acetate and megestrol acetate. It is an ester derivative of 17α-hydroxyprogesterone formed from caproic acid (hexanoic acid). Hydroxyprogesterone caproate was previously marketed under the trade name Delalutin by Squibb, which was approved by the U.S. Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. The U.S. FDA approved Makena from KV Pharmaceutical (previously named as Gestiva) on February 4, 2011 for prevention of preterm delivery in women with a history of preterm delivery, sparking a pricing controversy.

Structure
Thumb
Synonyms
17alpha-Caproyloxypregn-4-ene-3,20-dione
Delalutin
Hydroxyprogesterone
Oxiprogesterone Caproate
Primolut depot
External IDs NSC-17592
Product Ingredients
IngredientUNIICASInChI KeyDetails
hydroxyprogesterone caproateNot AvailableNot AvailableNot applicableDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MakenaInjection250 mg/mLIntramuscularAmag Pharmaceuticals Inc2011-02-03Not applicableUs
MakenaInjection250 mg/mLIntramuscularAmag Pharmaceuticals Inc2011-02-03Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydroxyprogesterone CaproateInjection250 mg/mLIntramuscularANI Pharmaceuticals, Inc.2016-06-03Not applicableUs
Hydroxyprogesterone CaproateInjection250 mg/mLIntramuscularMcguff Pharmaceuticals Inc2016-09-012017-04-14Us
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DelalutinBristol-Myers Squibb
GestivaCytyc
HormofortKobanyai
ldrogesteneFarmila
MakenaNot Available
Brand mixturesNot Available
Categories
UNII21807M87J2
CAS number630-56-8
WeightAverage: 428.6041
Monoisotopic: 428.292659768
Chemical FormulaC27H40O4
InChI KeyDOMWKUIIPQCAJU-LJHIYBGHSA-N
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
IUPAC Name
(1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl hexanoate
SMILES
[H][[email protected]@]12CC[[email protected]](OC(=O)CCCCC)(C(C)=O)[[email protected]@]1(C)CC[[email protected]@]1([H])[[email protected]@]2([H])CCC2=CC(=O)CC[[email protected]]12C
Pharmacology
Indication

Hydroxyprogesterone caproate is indicated for the prevention of spontaneous preterm births in singleton pregnancies in women who have previously had a spontaneous preterm birth. (1)

Structured Indications
Pharmacodynamics

No specific pharmacodynamic studies have been performed to assess hydroxyprogesterone caproate injections. (4) However, the mechanism of action is likely related to increased interaction between progesterone and progesterone receptors. (5)

Mechanism of action

The mechanism by which progesterone prevents preterm birth is not well understood, but many pathways are likely involved. (1) Progesterone plays a vital role in regulation of the female reproductive system and is important for successful implantation of the embryo and maintenance of pregnancy. It acts by binding to progesterone receptors in the uterus, ovaries, breasts and in the central nervous system. These receptors exist in 2 isoforms, PR-A and PR-B. Progesterone binding to these receptors ultimately leads to regulation of gene transcription. (2) This results in an anti-inflammatory effect which blunts the proinflammatory state that occurs with initiation of labor, and maintains uterine queiscence by stabilizing progesterone acting on the myometrium. (2)

TargetKindPharmacological actionActionsOrganismUniProt ID
Progesterone receptorProteinunknown
agonist
HumanP06401 details
Related Articles
Absorption

Absorption of 17-hydroxyprogesteron caproate is slow, occurring over a long period of time. (3)

Volume of distribution

Hydroxyprogesterone caproate has a high volume of distribution. (3)

Protein binding

Hydroxyprogesterone caproate is extensively protein bound in the plasma. (3)

Metabolism

The main enzymes involved in metabolism of hydroxyprogesterone caproate are cytochrome P450 (CYP) 3A4 and to a lesser extent CYP3A5. (3)

Route of elimination

Following intramuscular injection, approximately 50% of hydroxyprogesterone caproate metabolites are eliminated in the feces, while approximately 30% of metabolites are eliminated in the urine. (3)

Half life

Half-life = 16 days (±6 days). (3)

Clearance

Clearance is highly variable from patient to patient. (3)

Toxicity

Injection site pain is the most common adverse effect associated with hydroxyprogesterone caproate. Other commonly reported adverse effects include: injection site swelling, urticaria, pruritus, injection site pruritus, nausea, injection site nodule, and diarrhea. (4)

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of Thiazolidinedione can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Hydroxyprogesterone caproate.Withdrawn
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Approved
AICA ribonucleotideThe therapeutic efficacy of Aicar can be decreased when used in combination with Hydroxyprogesterone caproate.Experimental
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
AmiodaroneThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Amiodarone.Approved, Investigational
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
AprepitantThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
AtazanavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Atomoxetine.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Hydroxyprogesterone caproate.Approved, Investigational
BexaroteneThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
BoceprevirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Bosentan.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydroxyprogesterone caproate.Withdrawn
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Hydroxyprogesterone caproate.Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
CarbamazepineThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Carbamazepine.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Hydroxyprogesterone caproate.Experimental
CeritinibThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Ceritinib.Approved
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Experimental
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Hydroxyprogesterone caproate.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Cobicistat.Approved
Conestat alfaHydroxyprogesterone caproate may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
ConivaptanThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Hydroxyprogesterone caproate.Approved, Investigational
CyclosporineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
DabrafenibThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Withdrawn
DarexabanThe therapeutic efficacy of Ym150 can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
DarunavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Delavirdine.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Approved
DexamethasoneThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
DicoumarolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Approved
DihydroergotamineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Hydroxyprogesterone caproate.Approved, Investigational
DoxycyclineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Dronedarone.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
EfavirenzThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Efavirenz.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
EnzalutamideThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Hydroxyprogesterone caproate.Withdrawn
EtravirineThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Etravirine.Approved
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
FluconazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Fluconazole.Approved
FluindioneThe therapeutic efficacy of Fluindione can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
FluvoxamineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxThe therapeutic efficacy of Fondaparinux can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
FosamprenavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Fusidic Acid.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Hydroxyprogesterone caproate.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
Human C1-esterase inhibitorHydroxyprogesterone caproate may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
IdelalisibThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Idelalisib.Approved
IdraparinuxThe therapeutic efficacy of idraparinux can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
ImatinibThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Indinavir.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
IsavuconazoniumThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Ketoconazole.Approved, Investigational
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
LopinavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Lumacaftor.Approved
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
MifepristoneThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
MitotaneThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Modafinil.Approved, Investigational
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
NafcillinThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Nafcillin.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
NefazodoneThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Olaparib.Approved
OleandrinAnvirzel may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Experimental
OsimertinibThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Osimertinib.Approved
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Hydroxyprogesterone caproate.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Hydroxyprogesterone caproate.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Hydroxyprogesterone caproate.Approved, Vet Approved
PalbociclibThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Withdrawn
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
PhenobarbitalThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
PhenytoinThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
PosaconazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
PrimidoneThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Primidone.Approved, Vet Approved
Protein CThe therapeutic efficacy of Protein C can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
RanolazineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
RifabutinThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Hydroxyprogesterone caproate can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
SaquinavirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
SildenafilThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Simeprevir.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
St. John's WortThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
TelaprevirThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Telithromycin.Approved
TiclopidineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Tocilizumab.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Hydroxyprogesterone caproate.Approved, Investigational
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Withdrawn
UlipristalThe therapeutic efficacy of Hydroxyprogesterone caproate can be decreased when used in combination with Ulipristal.Approved
VenlafaxineThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Verapamil.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
VoriconazoleThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Hydroxyprogesterone caproate can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 2,753,360.

General References
  1. Goodnight W: Clinical Application of Progesterone for the Prevention of Preterm Birth, 2016. Am J Perinatol. 2016 Feb;33(3):253-7. doi: 10.1055/s-0035-1570378. Epub 2016 Jan 20. [PubMed:26788788 ]
  2. Ruan X, Mueck AO: Systemic progesterone therapy--oral, vaginal, injections and even transdermal? Maturitas. 2014 Nov;79(3):248-55. doi: 10.1016/j.maturitas.2014.07.009. Epub 2014 Jul 22. [PubMed:25113944 ]
  3. Feghali M, Venkataramanan R, Caritis S: Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22. doi: 10.1053/j.semperi.2014.08.013. Epub 2014 Sep 23. [PubMed:25256193 ]
  4. O'Brien JM, Lewis DF: Prevention of preterm birth with vaginal progesterone or 17-alpha-hydroxyprogesterone caproate: a critical examination of efficacy and safety. Am J Obstet Gynecol. 2016 Jan;214(1):45-56. doi: 10.1016/j.ajog.2015.10.934. Epub 2015 Nov 10. [PubMed:26558340 ]
External Links
ATC CodesG03DA03 — HydroxyprogesteroneG03FA02 — Hydroxyprogesterone and estrogen
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (383 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailablePregnancy1
1CompletedTreatmentComparing Bioavailability When Makena® is Administered in Healthy Post-menopausal Women1
2, 3CompletedPreventionPreterm Delivery1
3CompletedTreatmentAssessing Injection Pain of Makena® (Hydroxyprogesterone Caproate Injection, 250 mg/mL) in Healthy Post-menopausal Women1
3RecruitingPreventionPremature Births1
4RecruitingPreventionPremature Births1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
InjectionIntramuscular250 mg/mL
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)119-121U.S. Patent 2,753,360.
Predicted Properties
PropertyValueSource
Water Solubility0.000866 mg/mLALOGPS
logP4.81ALOGPS
logP5.88ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)17.81ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.69 m3·mol-1ChemAxon
Polarizability50.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aba-3940000000-835c32531e48d578d8eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative ParentsSteroid esters / 20-oxosteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Alpha-acyloxy ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
SubstituentsProgestogin-skeleton / Steroid ester / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Oxosteroid / Delta-4-steroid / Cyclohexenone / Alpha-acyloxy ketone / Carboxylic acid ester
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptorscorticosteroid hormone (CHEBI:5812 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Uniprot Name:
Progesterone receptor
Molecular Weight:
98979.96 Da
References
  1. O'Brien JM, Lewis DF: Prevention of preterm birth with vaginal progesterone or 17-alpha-hydroxyprogesterone caproate: a critical examination of efficacy and safety. Am J Obstet Gynecol. 2016 Jan;214(1):45-56. doi: 10.1016/j.ajog.2015.10.934. Epub 2015 Nov 10. [PubMed:26558340 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Uniprot Name:
Cytochrome P450 3A4
Molecular Weight:
57342.67 Da
References
  1. Feghali M, Venkataramanan R, Caritis S: Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22. doi: 10.1053/j.semperi.2014.08.013. Epub 2014 Sep 23. [PubMed:25256193 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Uniprot Name:
Cytochrome P450 3A5
Molecular Weight:
57108.065 Da
References
  1. Feghali M, Venkataramanan R, Caritis S: Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22. doi: 10.1053/j.semperi.2014.08.013. Epub 2014 Sep 23. [PubMed:25256193 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Uniprot Name:
Cytochrome P450 2C19
Molecular Weight:
55930.545 Da
References
  1. Feghali M, Venkataramanan R, Caritis S: Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22. doi: 10.1053/j.semperi.2014.08.013. Epub 2014 Sep 23. [PubMed:25256193 ]
Drug created on September 14, 2010 10:21 / Updated on September 01, 2017 11:31