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

Stem definition	Drug id	CAS RN
	56	59-66-5

Description:

Molecule

Description

Molfile Inchi Smiles Synonyms: acetazolamide acetamox acetazolamid cidamex nephramide acetazolamide sodium

One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337) Molecular weight: 222.24 Formula: C4H6N4O3S2 CLOGP: -0.98 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 115.04 ALOGS: -1.90 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Drug dosage:

Dose	Unit	Route
0.75	g	O
0.75	g	P

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	75.14 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.64 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	90 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.37 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.65 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.04 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	13 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
July 27, 1953	FDA	TEVA BRANDED 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
Drug ineffective	142.58	56.83	58	288	101566	2256173
Intraocular pressure increased	123.51	56.83	22	324	1487	2356252
Off label use	112.75	56.83	45	301	73553	2284186
Angle closure glaucoma	110.05	56.83	18	328	726	2357013
Metabolic acidosis	72.58	56.83	18	328	5980	2351759
Intellectual disability	70.95	56.83	10	336	143	2357596

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
Choroidal detachment	154.41	79.49	19	178	95	1746489
Intraocular pressure increased	116.88	79.49	20	177	1161	1745423
Angle closure glaucoma	105.55	79.49	15	182	250	1746334
Drug ineffective	97.73	79.49	38	159	63763	1682821
Choroidal effusion	86.51	79.49	11	186	73	1746511

Pharmacologic Action:

Source	Code	Description
ATC	S01EC01	SENSORY ORGANS OPHTHALMOLOGICALS ANTIGLAUCOMA PREPARATIONS AND MIOTICS Carbonic anhydrase inhibitors
FDA EPC	N0000175517	Carbonic Anhydrase Inhibitor
FDA CS	M0020790	Sulfonamides
MeSH PA	D000927	Anticonvulsants
MeSH PA	D002257	Carbonic Anhydrase Inhibitors
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D004232	Diuretics
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D045283	Natriuretic Agents

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Malignant glaucoma	indication	10100008
Anoxia due to high altitude	indication	42883007
Absence seizure	indication	79631006
Open-angle glaucoma	indication	84494001	DOID:1067
Secondary glaucoma	indication	95717004
Edema	indication	267038008
Peripheral edema	indication	271809000
Angle-closure glaucoma	indication	392291006	DOID:13550
Peripheral Edema due to Chronic Heart Failure	indication
Metabolic alkalosis	off-label use	1388004
Myoclonic seizure	off-label use	37356005
Benign intracranial hypertension	off-label use	68267002	DOID:11459
Epilepsy	off-label use	84757009	DOID:1826
Obstructive hydrocephalus	off-label use	230746009	DOID:14159
Familial periodic paralysis	off-label use	267607008	DOID:1029
Tonic-clonic epilepsy	off-label use	352818000	DOID:7725
Simple partial seizure	off-label use	117891000119100
Hydrocephalus due to Intraventricular Hemorrhage	off-label use
Mixed Epilepsy	off-label use
Urine Alkalinization	off-label use
Renal tubular acidosis	contraindication	1776003	DOID:14219
Respiratory acidosis	contraindication	12326000
Hyperkalemia	contraindication	14140009
Metabolic acidosis, normal anion gap, acidifying salts	contraindication	18104000
Diabetes mellitus type 2	contraindication	44054006	DOID:9352
Diabetes mellitus type 1	contraindication	46635009	DOID:9744
Acute nephropathy	contraindication	58574008
Hepatic failure	contraindication	59927004
Decreased respiratory function	contraindication	80954004
Hyponatremia	contraindication	89627008
Gout	contraindication	90560007	DOID:13189
Kidney disease	contraindication	90708001	DOID:557
Disease of blood AND/OR blood-forming organ	contraindication	191124002	DOID:74
Disease of liver	contraindication	235856003	DOID:409
Disorder of electrolytes	contraindication	237840007
Primary adrenocortical insufficiency	contraindication	373662000
Recurrent Calcium Renal Calculi	contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.04	acidic
pKa2	9.21	acidic
pKa3	1.84	Basic

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])	Mechanism action	Bioact source	MoA source
Carbonic anhydrase 12	Enzyme	O43570	CAH12_HUMAN	INHIBITOR	Ki	8.60		CHEMBL	CHEMBL
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN	INHIBITOR	Ki	7.96		CHEMBL	CHEMBL
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN	INHIBITOR	Ki	7.92		CHEMBL	CHEMBL
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN	INHIBITOR	Ki	8.48		CHEMBL	CHEMBL
Carbonic anhydrase 5A, mitochondrial	Enzyme	P35218	CAH5A_HUMAN		Ki	7.22		CHEMBL
Carbonic anhydrase	Enzyme	O43570 P00915 P00918 P07451 P22748 P23280 P35218 P43166 Q16790 Q8N1Q1 Q9ULX7 Q9Y2D0	CAH12_HUMAN CAH13_HUMAN CAH14_HUMAN CAH1_HUMAN CAH2_HUMAN CAH3_HUMAN CAH4_HUMAN CAH5A_HUMAN CAH5B_HUMAN CAH6_HUMAN CAH7_HUMAN CAH9_HUMAN		Ki	9.10		CHEMBL
Carbonic anhydrase 14	Enzyme	Q9ULX7	CAH14_HUMAN		Ki	7.39		CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	8.60		CHEMBL
Carbonic anhydrase 9	Enzyme	Q16790	CAH9_HUMAN		Ki	8.05		CHEMBL
Carbonic anhydrase V	Enzyme	P35218 Q9Y2D0	CAH5A_HUMAN CAH5B_HUMAN		Ki	8.74		CHEMBL
Carbonic anhydrase 5B, mitochondrial	Enzyme	Q9Y2D0	CAH5B_HUMAN		Ki	7.27		CHEMBL
Carbonic anhydrase 3	Enzyme	P07451	CAH3_HUMAN		Ki	8.51		CHEMBL
Carbonic anhydrase 13	Enzyme	Q8N1Q1	CAH13_HUMAN		Ki	8.24		CHEMBL
Carbonic anhydrase 6	Enzyme	P23280	CAH6_HUMAN		Ki	7.96		CHEMBL
Aquaporin-1	Transporter	P29972	AQP1_HUMAN					WOMBAT-PK
Carbonic anhydrase 2	Unclassified		Q3I4V7_CRYNV		Ki	8		CHEMBL
Carbonic anhydrase	Enzyme		CAN_YEAST		Ki	7.09		CHEMBL
Carbonic anhydrase	Unclassified		Q2PCB5_DICLA		Ki	5.24		CHEMBL
Carbonic anhydrase 2	Enzyme		CAH2_BOVIN		IC50	6.02		CHEMBL
Carbonic anhydrase	Enzyme		Q50565_METTH		Ki	4.92		CHEMBL
Carbonic anhydrase 13	Enzyme		CAH13_MOUSE		Ki	7.77		CHEMBL
Carbonic anhydrase	Enzyme		CYNT_HELPY		Ki	7.70		CHEMBL
Carbonic anhydrase 15	Enzyme		CAH15_MOUSE		Ki	7.14		CHEMBL
Alpha carbonic anhydrase	Unclassified		B5SU02_9CNID		Ki	7.80		CHEMBL
Carbonic anhydrase 7	Enzyme		CAH7_MOUSE		Ki	7.80		CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase	Enzyme		P96878_MYCTU		Ki	7.92		CHEMBL
Carbonic anhydrase	Enzyme		CAH2_BOVIN CAH3_BOVIN CAH4_BOVIN CAH6_BOVIN		IC50	7.80		CHEMBL
Endochitinase	Enzyme		CHIT_YEAST		Ki	4.68		CHEMBL
Carbonic anhydrase 3	Enzyme		CAH3_BOVIN		Ki	4.08		CHEMBL
Astrosclerin-3	Unclassified		A6YCJ1_9METZ		Ki	7.29		CHEMBL
Carbonic anhydrase	Enzyme		CAN_CANAL		Ki	7.40		CHEMBL
Carbonic anhydrase	Enzyme		CAH_METTE		Ki	7.22		CHEMBL
Beta-carbonic anhydrase 1	Enzyme		MTCA1_MYCTU		Ki	6.60		CHEMBL
Carbonic anhydrase 2	Enzyme		MTCA2_MYCTU		Ki	8.05		CHEMBL
Carbonic anhydrase	Enzyme		Q6FTL6_CANGA		Ki	7.96		CHEMBL
Carbonic anhydrase 4	Enzyme		CAH4_BOVIN		Ki	7.15		CHEMBL
Carbonic anhydrase	Enzyme		CAHX_FLABI		Ki	7.57		CHEMBL
Carbonic anhydrase	Unclassified		Q5TU56_ANOGA		Ki	7.56		CHEMBL
Carbonic anhydrase 1; GH09688p	Enzyme		Q9V396_DROME		Ki	6.97		CHEMBL
Carbonic anhydrase	Unclassified		Q9HVB9_PSEAE		Ki	7.12		CHEMBL
Carbonic anhydrase 2, isoform A; LD26647p	Enzyme		Q9VTU8_DROME		Ki	7.11		CHEMBL
Carbonic anhydrase	Unclassified		C0IX24_9CNID		Ki	7.13		CHEMBL
Delta carbonic anhydrase	Unclassified		Q5U9J1_THAWE		Ki	7.08		CHEMBL

External reference:

ID	Source
D000086	MESH_DESCRIPTOR_UI
4017898	VUID
N0000146250	NUI
C0000981	UMLSCUI
D00218	KEGG_DRUG
429ZT169UH	UNII
1424-27-7	SECONDARY_CAS_RN
33664007	SNOMEDCT_US
4017898	VANDF
814	MMSL
167	RXNORM
372709008	SNOMEDCT_US
4121	MMSL
d00161	MMSL
002286	NDDF
1986	PUBCHEM_CID
CHEBI:50634	CHEBI
CHEMBL20	ChEMBL_ID
DB00819	DRUGBANK_ID
CHEMBL1200814	ChEMBL_ID
481	INN_ID
6792	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9503	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	12 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1050	TABLET	250 mg	ORAL	ANDA	11 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0615-1511	TABLET	250 mg	ORAL	ANDA	12 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	0904-6663	TABLET	250 mg	ORAL	ANDA	11 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10135-567	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	23155-120	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	23155-287	TABLET	125 mg	ORAL	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	23155-288	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	29033-030	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	39822-0190	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	42291-089	TABLET	125 mg	ORAL	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	42291-090	TABLET	250 mg	ORAL	ANDA	11 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	42291-103	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	46708-349	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	11 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	50090-3003	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	50090-3132	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	50090-4511	TABLET	125 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	50742-233	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	51672-4022	TABLET	125 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	51672-4023	TABLET	250 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-1195	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	55289-720	TABLET	125 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	60429-033	TABLET	125 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	60429-034	TABLET	250 mg	ORAL	ANDA	12 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	62332-349	CAPSULE, EXTENDED RELEASE	500 mg	ORAL	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	63629-7889	TABLET	250 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	64380-833	TABLET	125 mg	ORAL	ANDA	11 sections
Acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	64380-834	TABLET	250 mg	ORAL	ANDA	11 sections
acetazolamide	HUMAN PRESCRIPTION DRUG LABEL	1	65841-762	CAPSULE	500 mg	ORAL	ANDA	11 sections
AcetaZOLAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	67296-0801	TABLET	250 1	ORAL	ANDA	11 sections