Hydrocortisone succinate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Hydrocortisone succinate is a corticosteroid used to treat severe allergic reactions, dermatologic diseases, endocrine disorders, gastrointestinal diseases, hematological disorders, neoplastic diseases, nervous system conditions, ophthalmic diseases, renal diseases, respiratory diseases, and rheumatic disorders.

Brand Names
Solu-cortef
Generic Name
Hydrocortisone succinate
DrugBank Accession Number
DB14545
Background

Not Available

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 462.539
Monoisotopic: 462.225368055
Chemical Formula
C25H34O8
Synonyms
  • Cortisol 21-(hydrogen succinate)
  • Cortisol succinate
  • Hydrocortisone hemisuccinate anhydrous
  • Hydrocortisone hydrogen succinate
  • Hydrocortisone succinate
  • Hydroxycortisone succinate

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAcquired hemolytic anemias•••••••••••••••••• •••••••• •••• ••••••••••••••••
Adjunct therapy in management ofAcute gouty arthritis•••••••••••••••••• •••••••• •••• ••••••••••••••••
Management ofAnkylosing spondylitis (as)•••••••••••••••••• •••••••• •••• ••••••••••••••••
Management ofBerylliosis•••••••••••••••••• •••••••• •••• ••••••••••••••••
Management ofBullous dermatitis herpetiformis•••••••••••••••••• •••••••• •••• ••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Hydrocortisone succinate can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Hydrocortisone succinate.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Hydrocortisone succinate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Hydrocortisone succinate.
AcarboseThe risk or severity of hyperglycemia can be increased when Hydrocortisone succinate is combined with Acarbose.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hydrocortisone sodium succinate50LQB69S1Z125-04-2HHZQLQREDATOBM-CODXZCKSSA-M
Hydrocortisone succinate monohydrateLIU00Z1Z8483784-20-7AFLWPAGYTPJSEY-CODXZCKSSA-N
Active Moieties
NameKindUNIICASInChI Key
HydrocortisoneunknownWI4X0X7BPJ50-23-7JYGXADMDTFJGBT-VWUMJDOOSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
A-hydrocort Inj 1000mg/8mlPowder, for solution1 g / vialIntramuscular; IntravenousHospira Healthcare Ulc1993-12-312012-08-03Canada flag
A-hydrocort Inj 100mg/2mlPowder, for solution100 mg / vialIntramuscular; IntravenousHospira Healthcare Ulc1992-12-312012-08-03Canada flag
A-hydrocort Inj 250mg/2mlPowder, for solution250 mg / vialIntramuscular; IntravenousHospira Healthcare Ulc1992-12-312012-08-03Canada flag
A-hydrocort Inj 500mg/4mlPowder, for solution500 mg / vialIntramuscular; IntravenousHospira Healthcare Ulc1992-12-312012-08-03Canada flag
Hydrocortisone Sodium Succinate for InjectionPowder, for solution500 mg / vialIntramuscular; IntravenousTEVA Canada Limited1994-12-312018-04-30Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
A-hydrocortInjection, powder, lyophilized, for solution100 mg/2mLIntramuscular; IntravenousHospira, Inc.2006-12-142010-07-01US flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
IHV1VP592V
CAS number
2203-97-6
InChI Key
VWQWXZAWFPZJDA-CGVGKPPMSA-N
InChI
InChI=1S/C25H34O8/c1-23-9-7-15(26)11-14(23)3-4-16-17-8-10-25(32,24(17,2)12-18(27)22(16)23)19(28)13-33-21(31)6-5-20(29)30/h11,16-18,22,27,32H,3-10,12-13H2,1-2H3,(H,29,30)/t16-,17-,18-,22+,23-,24-,25-/m0/s1
IUPAC Name
4-{2-[(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-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]-2-oxoethoxy}-4-oxobutanoic acid
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(=O)CCC(O)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

General References
Not Available
KEGG Drug
D01442
ChemSpider
15760
BindingDB
50016931
RxNav
21651
ChEBI
31677
ChEMBL
CHEMBL977
ZINC
ZINC000004097472
Wikipedia
Hydrocortisone_hemisuccinate

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedTreatmentCongenital Adrenal Hyperplasia (CAH)1somestatusstop reasonjust information to hide
Not AvailableRecruitingTreatmentHealthcare-associated Pneumonia (HCAP) / Ventilator Associated Bacterial Pneumonia (VABP)1somestatusstop reasonjust information to hide
Not AvailableRecruitingTreatmentIntussusception (IS)1somestatusstop reasonjust information to hide
Not AvailableSuspendedNot AvailableSome Studies Shows That the Steroid Can Reduce the Injury of the I/R of the Liver1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusPreventionAdrenal Insufficiency / Pituitary Adenoma / Surgery1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous100 mg/2mL
Injection, powder, for solution100 mg
SolutionIntravenous134.00 mg
InjectionIntramuscular; Intravenous100 mg
Injection; injection, powder, for solutionIntramuscular; Intravenous100 mg
Powder, for solutionIntramuscular; Intravenous100 mg / vial
Powder, for solutionIntramuscular; Intravenous250 mg / vial
Powder, for solutionIntramuscular; Intravenous500 mg / vial
Powder100 mg/1vial
Powder, for solutionIntramuscular; Intravenous1 g / vial
Injection, powder, for solution134 mg
SolutionAuricular (otic)
Injection, powder, lyophilized, for solutionIntravenous100 mg
Injection, powder, for solutionIntramuscular; Intravascular100 mg/2mL
Injection, powder, for solutionIntramuscular; Intravascular1000 mg/8mL
Injection, powder, for solutionIntramuscular; Intravascular250 mg/2mL
Injection, powder, for solutionIntramuscular; Intravascular500 mg/4mL
Injection, powder, for solutionIntramuscular; Intravenous100 mg/2mL
Injection, powder, for solutionIntramuscular; Intravenous1000 mg/8mL
Injection, powder, for solutionIntramuscular; Intravenous250 mg/2mL
Injection, powder, for solutionIntramuscular; Intravenous500 mg/4mL
Injection, powder, for solutionIntramuscular; Intravenous100 mg
InjectionIntramuscular; Intravenous
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0653 mg/mLALOGPS
logP2.17ALOGPS
logP1.54Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.66Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area138.2 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity117.44 m3·mol-1Chemaxon
Polarizability48.68 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-0004900000-e530faeb68007ef36ea0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-003s-1009000000-52019723ed10df964359
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-3525900000-842096195ef2b1ea2929
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-3009000000-9502a41e3c151e29e4c5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-1925100000-63c659c826d00d1e15d3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9004100000-e03286a590f5c34f5717
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-228.8830037
predicted
DarkChem Lite v0.1.0
[M+H]+226.7988037
predicted
DarkChem Lite v0.1.0
[M+Na]+225.8376037
predicted
DarkChem Lite v0.1.0

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Joellenbeck L, Qian Z, Zarba A, Groopman JD: Urinary 6 beta-hydroxycortisol/cortisol ratios measured by high-performance liquid chromatography for use as a biomarker for the human cytochrome P-450 3A4. Cancer Epidemiol Biomarkers Prev. 1992 Nov-Dec;1(7):567-72. [Article]
  2. Litt J. (2016). Litt's Drug eruption & reaction manual (22nd ed.). CRC Press LLc.
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function
Arachidonic acid epoxygenase activity
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Bauersachs J, Christ M, Ertl G, Michaelis UR, Fisslthaler B, Busse R, Fleming I: Cytochrome P450 2C expression and EDHF-mediated relaxation in porcine coronary arteries is increased by cortisol. Cardiovasc Res. 2002 Jun;54(3):669-75. [Article]
  2. Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Catalyzes a variety of reactions that are essential for many species, including detoxification, defense, and the formation of endogenous chemicals like steroid hormones. Steroid 11beta, 18- and 19-hydroxylase with preferred regioselectivity at 11beta, then 18, and lastly 19 (By similarity). Catalyzes the hydroxylation of 11-deoxycortisol and 11-deoxycorticosterone (21-hydroxyprogesterone) at 11beta position, yielding cortisol or corticosterone, respectively, but cannot produce aldosterone (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate for hydroxylation and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:18215163). Due to its lack of 18-oxidation activity, it is incapable of generating aldosterone (PubMed:23322723). Could also be involved in the androgen metabolic pathway (Probable)
Specific Function
Corticosterone 18-monooxygenase activity
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
Cytochrome P450 11B1, mitochondrial
Molecular Weight
57572.44 Da
References
  1. Freel EM, Shakerdi LA, Friel EC, Wallace AM, Davies E, Fraser R, Connell JM: Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. J Clin Endocrinol Metab. 2004 Sep;89(9):4628-33. doi: 10.1210/jc.2004-0379. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
A cytochrome P450 monooxygenase that catalyzes the biosynthesis of aldosterone, the main mineralocorticoid in the human body responsible for salt and water homeostasis, thus involved in blood pressure regulation, arterial hypertension, and the development of heart failure (PubMed:11856349, PubMed:12530636, PubMed:1518866, PubMed:15356073, PubMed:1594605, PubMed:1775135, PubMed:22446688, PubMed:23322723, PubMed:9814482, PubMed:9814506). Catalyzes three sequential oxidative reactions of 11-deoxycorticosterone (21-hydroxyprogesterone), namely 11-beta hydroxylation, followed by two successive oxidations at C18 yielding 18-hydroxy and then 18-oxo intermediates (that would not leave the enzyme active site during the consecutive hydroxylation reactions), ending with the formation of aldosterone (PubMed:11856349, PubMed:12530636, PubMed:1518866, PubMed:1594605, PubMed:1775135, PubMed:22446688, PubMed:23322723, PubMed:9814506). Can also produce 18-hydroxycortisol and 18-oxocortisol, derived from successive oxidations of cortisol at C18, normally found at very low levels, but significantly increased in primary aldosteronism, the most common form of secondary hypertension (PubMed:15356073, PubMed:9814482). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11856349, PubMed:1594605, PubMed:23322723, PubMed:9814506). Could also be involved in the androgen metabolic pathway (Probable)
Specific Function
Corticosterone 18-monooxygenase activity
Gene Name
CYP11B2
Uniprot ID
P19099
Uniprot Name
Cytochrome P450 11B2, mitochondrial
Molecular Weight
57559.62 Da
References
  1. Freel EM, Shakerdi LA, Friel EC, Wallace AM, Davies E, Fraser R, Connell JM: Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. J Clin Endocrinol Metab. 2004 Sep;89(9):4628-33. doi: 10.1210/jc.2004-0379. [Article]

Drug created at July 12, 2018 21:25 / Updated at September 15, 2024 21:55