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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
Cardiac failure congestive	69.11	13.80	91	9808	91659	46584504
Segmental diverticular colitis	65.83	13.80	13	9886	130	46676033
Pedal pulse abnormal	64.87	13.80	13	9886	141	46676022
Blood pressure abnormal	64.04	13.80	37	9862	12180	46663983
Toxic epidermal necrolysis	63.51	13.80	46	9853	22232	46653931
Calcium ionised decreased	58.44	13.80	13	9886	240	46675923
Insulin autoimmune syndrome	49.78	13.80	9	9890	53	46676110
Feeding intolerance	49.38	13.80	13	9886	497	46675666
Occupational exposure to product	48.68	13.80	17	9882	1704	46674459
Multiple organ dysfunction syndrome	48.03	13.80	57	9842	51653	46624510
Cardiac failure	40.79	13.80	66	9833	79882	46596281
Labile hypertension	40.00	13.80	11	9888	497	46675666
Left ventricular hypertrophy	37.04	13.80	19	9880	4944	46671219
Hypertension	36.81	13.80	108	9791	196248	46479915
Myocardial infarction	32.55	13.80	67	9832	97461	46578702
Haemodynamic instability	31.70	13.80	20	9879	7705	46668458
Self-injurious ideation	30.18	13.80	13	9886	2287	46673876
Metabolic acidosis	29.98	13.80	39	9860	38741	46637422
Hypotension	29.38	13.80	112	9787	232477	46443686
Dermatitis exfoliative	29.12	13.80	17	9882	5699	46670464
Rheumatoid arthritis	28.22	13.80	8	9891	240207	46435956
Gastrointestinal sounds abnormal	24.95	13.80	13	9886	3493	46672670
Electrolyte imbalance	24.86	13.80	24	9875	17202	46658961
Hyperthyroidism	24.22	13.80	20	9879	11691	46664472
Cardiac failure acute	23.74	13.80	17	9882	8061	46668102
Blood urea increased	23.61	13.80	28	9871	25324	46650839
Hypertensive crisis	23.58	13.80	21	9878	13594	46662569
Skin test positive	23.53	13.80	8	9891	740	46675423
Acute myocardial infarction	22.97	13.80	31	9868	31893	46644270
Vascular stent thrombosis	22.34	13.80	8	9891	863	46675300
Renal failure	20.78	13.80	62	9837	113532	46562631
Renal injury	19.12	13.80	16	9883	9525	46666638
Stevens-Johnson syndrome	18.90	13.80	24	9875	23273	46652890
Respiratory disorder	18.87	13.80	26	9873	27274	46648889
Cholecystitis	18.73	13.80	19	9880	14447	46661716
Hyperkalaemia	18.29	13.80	36	9863	50673	46625490
Progressive supranuclear palsy	18.24	13.80	4	9895	69	46676094
Acute kidney injury	18.06	13.80	98	9801	235757	46440406
Posterior reversible encephalopathy syndrome	18.01	13.80	19	9880	15122	46661041
Artery dissection	17.45	13.80	4	9895	85	46676078
Drug interaction	17.34	13.80	87	9812	203007	46473156
Circulatory collapse	17.10	13.80	22	9877	21602	46654561
Nodal rhythm	17.05	13.80	8	9891	1717	46674446
Renal impairment	16.96	13.80	44	9855	74328	46601835
Extrasystoles	16.06	13.80	11	9888	4858	46671305
Potentiating drug interaction	15.70	13.80	10	9889	3913	46672250
Arthralgia	15.47	13.80	34	9865	364569	46311594
Cyanosis	15.47	13.80	18	9881	15953	46660210
Shock	15.39	13.80	21	9878	21824	46654339
Blister	15.27	13.80	31	9868	44600	46631563
Blood creatinine increased	15.21	13.80	43	9856	76360	46599803
Bradycardia	14.89	13.80	39	9860	66259	46609904
Coronary artery disease	14.72	13.80	26	9873	33726	46642437
Cholelithiasis	14.60	13.80	28	9871	38653	46637510
Product dose omission issue	14.36	13.80	9	9890	168511	46507652
Restlessness	14.28	13.80	22	9877	25502	46650661
Occupational dermatitis	14.13	13.80	3	9896	44	46676119
Dehydration	14.08	13.80	69	9830	159471	46516692
Fatigue	14.06	13.80	74	9825	608623	46067540

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
Blood ketone body increased	36.54	14.49	10	7699	364	29944405
Scleroderma renal crisis	31.93	14.49	7	7702	98	29944671
Cyanosis	28.44	14.49	24	7685	11911	29932858
Cardiac failure congestive	28.08	14.49	65	7644	84342	29860427
Angioedema	27.75	14.49	39	7670	34345	29910424
Hypertensive crisis	24.56	14.49	19	7690	8338	29936431
Kidney small	23.01	14.49	5	7704	67	29944702
Renal failure	21.97	14.49	78	7631	128888	29815881
Long QT syndrome	21.60	14.49	11	7698	2322	29942447
Vitamin B12 deficiency	20.45	14.49	11	7698	2594	29942175
Bladder sphincter atony	19.72	14.49	3	7706	3	29944766
Myocardial infarction	18.89	14.49	73	7636	125552	29819217
Indifference	18.89	14.49	5	7704	160	29944609
Colitis microscopic	18.64	14.49	9	7700	1694	29943075
Hypertension	18.64	14.49	71	7638	121283	29823486
Pulmonary hypertensive crisis	18.62	14.49	5	7704	169	29944600
Reaction to excipient	18.56	14.49	6	7703	390	29944379
Coronary artery disease	18.44	14.49	40	7669	49672	29895097
Cardiac failure	18.28	14.49	55	7654	83363	29861406
Cerebrovascular accident	18.26	14.49	55	7654	83422	29861347
Hypokalaemia	18.18	14.49	40	7669	50152	29894617
Blood creatinine increased	17.95	14.49	58	7651	91317	29853452
Renal failure neonatal	16.81	14.49	4	7705	82	29944687
Haemorrhagic necrotic pancreatitis	16.63	14.49	4	7705	86	29944683
Vascular resistance systemic decreased	16.13	14.49	4	7705	98	29944671
Bronchospasm	15.38	14.49	16	7693	10322	29934447
Orthopnoea	14.84	14.49	11	7698	4529	29940240
Klebsiella infection	14.68	14.49	13	7696	6874	29937895

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 MoA	N0000000181	Angiotensin-converting Enzyme Inhibitors
FDA EPC	N0000175562	Angiotensin Converting Enzyme Inhibitor
CHEBI has role	CHEBI:35457	ace inhibitor
CHEBI has role	CHEBI:35674	antihypertensive
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
4017614	VUID
N0000145994	NUI
D00251	KEGG_DRUG
4017614	VANDF
C0006938	UMLSCUI
CHEBI:3380	CHEBI
X8Z	PDB_CHEM_ID
2550	PUBCHEM_CID
CHEMBL1560	ChEMBL_ID
DB01197	DRUGBANK_ID
D002216	MESH_DESCRIPTOR_UI
4373	INN_ID
5158	IUPHAR_LIGAND_ID
9G64RSX1XD	UNII
1998	RXNORM
4347	MMSL
455	MMSL
d00006	MMSL
000656	NDDF
29439004	SNOMEDCT_US
387160004	SNOMEDCT_US

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	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1172	TABLET	25 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1173	TABLET	50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0143-1174	TABLET	100 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3007	TABLET	12.50 mg	ORAL	ANDA	25 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3012	TABLET	25 mg	ORAL	ANDA	25 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3017	TABLET	50 mg	ORAL	ANDA	25 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3022	TABLET	100 mg	ORAL	ANDA	25 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4519	TABLET	12.50 mg	ORAL	ANDA	21 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4520	TABLET	25 mg	ORAL	ANDA	21 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0615-4521	TABLET	50 mg	ORAL	ANDA	21 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8052	TABLET	12.50 mg	ORAL	ANDA	16 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8061	TABLET	25 mg	ORAL	ANDA	16 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8075	TABLET	50 mg	ORAL	ANDA	16 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0781-8080	TABLET	100 mg	ORAL	ANDA	16 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5045	TABLET	12.50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5046	TABLET	25 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5047	TABLET	50 mg	ORAL	ANDA	22 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7105	TABLET	12.50 mg	ORAL	ANDA	12 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7106	TABLET	25 mg	ORAL	ANDA	12 sections
CAPTOPRIL	HUMAN PRESCRIPTION DRUG LABEL	1	10544-175	TABLET	50 mg	ORAL	ANDA	19 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	21695-477	TABLET	25 mg	ORAL	ANDA	24 sections
Captopril	HUMAN PRESCRIPTION DRUG LABEL	1	21695-478	TABLET	50 mg	ORAL	ANDA	24 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	19 sections
CAPTOPRIL	HUMAN PRESCRIPTION DRUG LABEL	1	33261-536	TABLET	100 mg	ORAL	ANDA	19 sections
CAPTOPRIL	HUMAN PRESCRIPTION DRUG LABEL	1	33261-974	TABLET	25 mg	ORAL	ANDA	19 sections