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captopril Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
angiotensin-converting enzyme inhibitors	484	62571-86-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: captopril (-)-Captopril L-Captopril lopirin S-Captopril SQ14225 SQ-14225 SQ 14225	A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin. Molecular weight: 217.28 Formula: C9H15NO3S CLOGP: 0.89 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 57.61 ALOGS: -1.68 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

captopril
(-)-Captopril
L-Captopril
lopirin
S-Captopril
SQ14225
SQ-14225
SQ 14225

A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.

Molecular weight: 217.28
Formula: C9H15NO3S
CLOGP: 0.89
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 57.61
ALOGS: -1.68
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
50	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	160 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	38 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	19.72 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	69 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.75 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	12 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.73 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	2 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
April 6, 1981	FDA	PAR PHARM

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hypotension	146.61	56.03	45	318	32391	2325331
Toxic epidermal necrolysis	124.09	56.03	25	338	3119	2354603
Multiple organ dysfunction syndrome	117.49	56.03	28	335	7613	2350109
Hyperthyroidism	102.76	56.03	20	343	2077	2355645
Acute kidney injury	97.41	56.03	32	331	28090	2329632
Electrolyte imbalance	97.17	56.03	19	344	2018	2355704
Cholecystitis	95.37	56.03	19	344	2221	2355501
Respiratory disorder	84.37	56.03	19	344	3985	2353737
Cholelithiasis	82.48	56.03	20	343	5783	2351939
Condition aggravated	81.70	56.03	29	334	31950	2325772
Dermatitis exfoliative	80.51	56.03	15	348	1226	2356496
Suicide attempt	78.35	56.03	22	341	11260	2346462
Insulin autoimmune syndrome	76.54	56.03	9	354	23	2357699
Diarrhoea	75.83	56.03	36	327	83528	2274194
Posterior reversible encephalopathy syndrome	70.15	56.03	15	348	2465	2355257
Restlessness	66.17	56.03	16	347	4547	2353175
Angioedema	65.70	56.03	18	345	8378	2349344
Blister	59.90	56.03	16	347	6755	2350967
Hypertension	59.19	56.03	22	341	27339	2330383
Renal impairment	57.97	56.03	17	346	10075	2347647
Nausea	57.47	56.03	33	330	112156	2245566
Erythema	57.23	56.03	21	342	25138	2332584
Cardiac failure acute	57.01	56.03	11	352	1078	2356644

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Angioedema	89.21	43.53	25	268	9639	1736849
Hypotension	72.33	43.53	28	265	29626	1716862
Blood ketone body increased	63.63	43.53	9	284	92	1746396
Hyperkalaemia	60.35	43.53	18	275	8529	1737959
Acute kidney injury	51.19	43.53	23	270	34921	1711567
Hypertension	45.84	43.53	18	275	19430	1727058

Pharmacologic Action:

Source	Code	Description
ATC	C09AA01	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, PLAIN ACE inhibitors, plain
ATC	C09BA01	CARDIOVASCULAR SYSTEM AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM ACE INHIBITORS, COMBINATIONS ACE inhibitors and diuretics
FDA EPC	N0000175562	Angiotensin Converting Enzyme Inhibitor
CHEBI has role	CHEBI:35457	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
CHEBI has role	CHEBI:35674	antihypertensive agent
MeSH PA	D000806	Angiotensin-Converting Enzyme Inhibitors
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D011480	Protease Inhibitors

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Hypertensive disorder	indication	38341003	DOID:10763
Chronic heart failure	indication	48447003
Diabetic renal disease	indication	127013003
Left ventricular cardiac dysfunction	indication	429589006
Atrial fibrillation	off-label use	49436004	DOID:0060224
Cystinuria	off-label use	85020001	DOID:9266
Diastolic heart failure	off-label use	418304008	DOID:9775
Cystine Renal Calculi	off-label use
Nondiabetic Proteinuric Nephropathy	off-label use
Anuria	contraindication	2472002	DOID:2983
Hypercholesterolemia	contraindication	13644009
Hyperkalemia	contraindication	14140009
Secondary angle-closure glaucoma	contraindication	21571006
Hypovolemia	contraindication	28560003
Acute cerebrovascular insufficiency	contraindication	29322000
Dehydration	contraindication	34095006
Hyperuricemia	contraindication	35885006	DOID:1920
Immunosuppression	contraindication	38013005
Angioedema	contraindication	41291007	DOID:1558
Hypokalemia	contraindication	43339004
Low blood pressure	contraindication	45007003
Cough	contraindication	49727002
Systemic lupus erythematosus	contraindication	55464009	DOID:9074
Sympathectomy	contraindication	57071006
Aortic valve stenosis	contraindication	60573004	DOID:1712
Hypercalcemia	contraindication	66931009	DOID:12678
Hyperparathyroidism	contraindication	66999008	DOID:13543
Hypochloremic alkalosis	contraindication	70134007
Hepatic coma	contraindication	72836002	DOID:12550
Diabetes mellitus	contraindication	73211009	DOID:9351
Transplantation	contraindication	77465005
Hereditary angioneurotic edema	contraindication	82966003	DOID:14735
Hyponatremia	contraindication	89627008
Gout	contraindication	90560007	DOID:13189
Kidney disease	contraindication	90708001	DOID:557
Disorder of connective tissue	contraindication	105969002	DOID:65
Hypomagnesemia	contraindication	190855004
Acute pancreatitis	contraindication	197456007	DOID:2913
Hypertrophic cardiomyopathy	contraindication	233873004	DOID:11984
Disease of liver	contraindication	235856003	DOID:409
Neonatal hyperbilirubinemia	contraindication	281610001
Pregnancy, function	contraindication	289908002
Renal artery stenosis	contraindication	302233006
Neutropenic disorder	contraindication	303011007	DOID:1227
Bone marrow depression	contraindication	307762000
Azotemia	contraindication	445009001
Hemodialysis with High-Flux Membrane	contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.85	acidic
pKa2	9.56	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Angiotensin-converting enzyme	Enzyme	P12821	ACE_HUMAN	INHIBITOR	Ki	8.70	WOMBAT-PK	CHEMBL
Prothrombin	Enzyme	P00734	THRB_HUMAN		Ki	7.32	CHEMBL
Leukotriene A-4 hydrolase	Enzyme	P09960	LKHA4_HUMAN		IC50	7.15	CHEMBL
Prostaglandin G/H synthase 1	Enzyme	P23219	PGH1_HUMAN		Ki	4.77	CHEMBL
Renin	Enzyme	P00797	RENI_HUMAN		Ki	8.77	CHEMBL
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN		Ki	4.92	CHEMBL
Beta-lactamase	Enzyme		Q79MP6_PSEAI		Ki	5.62	CHEMBL
Angiotensin-converting enzyme	Enzyme		ACE_RABIT		Ki	8.77	CHEMBL
Angiotensin-converting enzyme	Enzyme		ACE_RAT		Ki	8.70	CHEMBL
Succinyl-diaminopimelate desuccinylase	Enzyme		DAPE_HAEIN		Ki	5.74	CHEMBL
Beta-lactamase II	Unclassified		Q93T40_BACAN		Ki	4.75	CHEMBL
Beta-lactamase class B VIM-2	Unclassified		Q9K2N0_PSEAI		Kd	6.22	CHEMBL

External reference:

ID	Source
D002216	MESH_DESCRIPTOR_UI
4017614	VUID
N0000145994	NUI
C0006938	UMLSCUI
D00251	KEGG_DRUG
29439004	SNOMEDCT_US
4017614	VANDF
000656	NDDF
455	MMSL
1998	RXNORM
387160004	SNOMEDCT_US
4347	MMSL
d00006	MMSL
9G64RSX1XD	UNII
4373	INN_ID
44093	PUBCHEM_CID
CHEBI:3380	CHEBI
CHEMBL1560	ChEMBL_ID
X8Z	PDB_CHEM_ID
DB01197	DRUGBANK_ID
5158	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1171	TABLET	12.50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1172	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1173	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1174	TABLET	100 mg	ORAL	ANDA	12 sections
Captopril and Hydrochlorothiazide	HUMAN PRESCRIPTION DRUG LABEL	2	0378-0081	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril and Hydrochlorothiazide	HUMAN PRESCRIPTION DRUG LABEL	2	0378-0083	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril and Hydrochlorothiazide	HUMAN PRESCRIPTION DRUG LABEL	2	0378-0084	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril and Hydrochlorothiazide	HUMAN PRESCRIPTION DRUG LABEL	2	0378-0086	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3007	TABLET	12.50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3012	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3017	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3022	TABLET	100 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4519	TABLET	12.50 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4520	TABLET	25 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4521	TABLET	50 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8052	TABLET	12.50 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8061	TABLET	25 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8075	TABLET	50 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8080	TABLET	100 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5045	TABLET	12.50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5046	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5047	TABLET	50 mg	ORAL	ANDA	12 sections
CAPTOPRIL	HUMAN PRESCRIPTION DRUG LABEL	1	10544-175	TABLET	50 mg	ORAL	ANDA	13 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	21695-477	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	21695-478	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	27241-160	TABLET	12.50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	27241-161	TABLET	25 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	27241-162	TABLET	50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	27241-163	TABLET	100 mg	ORAL	ANDA	12 sections
CAPTOPRIL	HUMAN PRESCRIPTION DRUG LABEL	1	33261-182	TABLET	50 mg	ORAL	ANDA	13 sections