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

Stem definition	Drug id	CAS RN
	949	120279-96-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: dorzolamide dorzolamide hydrochloride dorzolamide HCl	topically effective ocular hypotensive carbonic anhydrase inhibitor; RN refers to mono-HCl (4S-trans)-isomer Molecular weight: 324.43 Formula: C10H16N2O4S3 CLOGP: 0.15 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 106.33 ALOGS: -2.67 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

dorzolamide
dorzolamide hydrochloride
dorzolamide HCl

topically effective ocular hypotensive carbonic anhydrase inhibitor; RN refers to mono-HCl (4S-trans)-isomer

Molecular weight: 324.43
Formula: C10H16N2O4S3
CLOGP: 0.15
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 106.33
ALOGS: -2.67
ROTB: 3

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.30	ml	None

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	3.90 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	10 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	3.08 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

Date	Agency	Company	Orphan
Dec. 9, 1994	FDA	MERCK

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
Eye irritation	509.48	51.89	92	604	3420	2353969
Intraocular pressure increased	341.88	51.89	58	638	1451	2355938
Ocular hyperaemia	209.01	51.89	45	651	4011	2353378
Eye pain	189.69	51.89	43	653	4848	2352541
Drug ineffective	181.01	51.89	85	611	101539	2255850
Product quality issue	174.50	51.89	47	649	10782	2346607
Glaucoma	134.89	51.89	28	668	2067	2355322
Vision blurred	100.78	51.89	33	663	14635	2342754
No adverse event	92.77	51.89	28	668	9500	2347889
Visual acuity reduced	85.00	51.89	23	673	5275	2352114
Eye pruritus	75.28	51.89	18	678	2513	2354876
Product dose omission	73.17	51.89	34	662	38223	2319166
Hand deformity	72.61	51.89	15	681	1071	2356318
Eye discharge	69.07	51.89	14	682	909	2356480
Ocular surface disease	66.43	51.89	8	688	10	2357379
Dyspnoea	62.61	51.89	39	657	78694	2278695
Sciatica	62.59	51.89	15	681	2110	2355279
Eye swelling	60.83	51.89	17	679	4373	2353016
Product packaging quantity issue	54.55	51.89	10	686	380	2357009
Choroidal detachment	54.31	51.89	8	688	74	2357315
Drug hypersensitivity	52.50	51.89	29	667	46614	2310775

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
Intraocular pressure increased	339.01	69.84	57	452	1124	1745148
Eye irritation	295.28	69.84	52	457	1351	1744921
Ocular hyperaemia	148.23	69.84	31	478	1979	1744293
Eye pain	132.40	69.84	29	480	2302	1743970
Visual acuity reduced	97.62	69.84	25	484	3863	1742409
Product quality issue	86.49	69.84	25	484	6068	1740204
Eye pruritus	79.44	69.84	16	493	834	1745438
Drug ineffective	77.00	69.84	44	465	63757	1682515

Pharmacologic Action:

Source	Code	Description
ATC	S01EC03	SENSORY ORGANS OPHTHALMOLOGICALS ANTIGLAUCOMA PREPARATIONS AND MIOTICS Carbonic anhydrase inhibitors
CHEBI has role	CHEBI:35674	antihypertensive agent
CHEBI has role	CHEBI:39456	antiglaucoma drug
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002257	Carbonic Anhydrase Inhibitors
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors
FDA EPC	N0000175517	Carbonic Anhydrase Inhibitor

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Ocular hypertension	indication	4210003	DOID:9282
Open-angle glaucoma	indication	84494001	DOID:1067
Bronchospasm	contraindication	4386001
Complete atrioventricular block	contraindication	27885002
Acute cerebrovascular insufficiency	contraindication	29322000
Hyperthyroidism	contraindication	34486009	DOID:7998
Anaphylaxis	contraindication	39579001
Sinus bradycardia	contraindication	49710005
General anesthesia	contraindication	50697003
Acute nephropathy	contraindication	58574008
Diabetes mellitus	contraindication	73211009	DOID:9351
Pulmonary emphysema	contraindication	87433001
Cardiogenic shock	contraindication	89138009
Myasthenia gravis	contraindication	91637004	DOID:437
Partial atrioventricular block	contraindication	195039008
Decompensated cardiac failure	contraindication	195111005
Hypoglycemic disorder	contraindication	237630007
Pregnancy, function	contraindication	289908002
Severe chronic obstructive pulmonary disease	contraindication	313299006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.73	acidic
pKa2	8.34	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])	Bioact source	MoA source
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN	INHIBITOR	Ki	9.70	CHEMBL	CHEMBL
Carbonic anhydrase 12	Enzyme	O43570	CAH12_HUMAN		Ki	8.46	CHEMBL
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN		Ki	7.37	CHEMBL
Carbonic anhydrase 13	Enzyme	Q8N1Q1	CAH13_HUMAN		Ki	7.74	CHEMBL
Carbonic anhydrase 3	Enzyme	P07451	CAH3_HUMAN		Ki	5.10	CHEMBL
Carbonic anhydrase 5A, mitochondrial	Enzyme	P35218	CAH5A_HUMAN		Ki	7.38	CHEMBL
Carbonic anhydrase 14	Enzyme	Q9ULX7	CAH14_HUMAN		Ki	7.57	CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	8.46	CHEMBL
Carbonic anhydrase 9	Enzyme	Q16790	CAH9_HUMAN		Ki	7.28	CHEMBL
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN		Ki	6.30	CHEMBL
Carbonic anhydrase 5B, mitochondrial	Enzyme	Q9Y2D0	CAH5B_HUMAN		Ki	7.48	CHEMBL
Carbonic anhydrase 6	Enzyme	P23280	CAH6_HUMAN		Ki	8	CHEMBL
Carbonic anhydrase 13	Enzyme		CAH13_MOUSE		Ki	7.74	CHEMBL
Carbonic anhydrase	Enzyme		Q50565_METTH		Ki	4.51	CHEMBL
Alpha carbonic anhydrase	Unclassified		B5SU02_9CNID		Ki	7.74	CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase	Enzyme		P96878_MYCTU		Ki	6.86	CHEMBL
Astrosclerin-3	Unclassified		A6YCJ1_9METZ		Ki	6.55	CHEMBL
Beta-carbonic anhydrase 1	Enzyme		MTCA1_MYCTU		Ki	6.13	CHEMBL
Carbonic anhydrase	Unclassified		C0IX24_9CNID		Ki	6.95	CHEMBL
Delta carbonic anhydrase	Unclassified		Q5U9J1_THAWE		Ki	7.30	CHEMBL
Carbonic anhydrase	Enzyme		CAN_YEAST		Ki	6.96	CHEMBL
Carbonic anhydrase	Enzyme		CYNT_HELPY		Ki	5.37	CHEMBL
Carbonic anhydrase 15	Enzyme		CAH15_MOUSE		Ki	7.21	CHEMBL
Carbonic anhydrase	Enzyme		CAN_CANAL		Ki	8.05	CHEMBL
Carbonic anhydrase	Enzyme		CAH_METTE		Ki	6.39	CHEMBL
Carbonic anhydrase 2	Enzyme		MTCA2_MYCTU		Ki	7	CHEMBL
Carbonic anhydrase 4	Enzyme		CAH4_BOVIN		Ki	7.37	CHEMBL
Carbonic anhydrase	Unclassified		Q5TU56_ANOGA		Ki	6.56	CHEMBL
Carbonic anhydrase	Enzyme		Q6FTL6_CANGA		Ki	5.18	CHEMBL

External reference:

ID	Source
4023982	VUID
N0000021987	NUI
C0165590	UMLSCUI
D00653	KEGG_DRUG
108834004	SNOMEDCT_US
4023982	VANDF
60207	RXNORM
373447009	SNOMEDCT_US
004998	NDDF
9JDX055TW1	UNII
6960	INN_ID
CHEMBL218490	ChEMBL_ID
DB00869	DRUGBANK_ID
130693-82-2	SECONDARY_CAS_RN
ETS	PDB_CHEM_ID
CHEBI:4702	CHEBI
6810	IUPHAR_LIGAND_ID
5284549	PUBCHEM_CID
CHEMBL1201162	ChEMBL_ID
C062765	MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
TRUSOPT	HUMAN PRESCRIPTION DRUG LABEL	1	0006-3519	SOLUTION	20 mg	OPHTHALMIC	NDA	18 sections
Dorzolamide Hydrochloride-Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	0527-1763	SOLUTION	20 mg	OPHTHALMIC	ANDA	13 sections
Dorzolamide HCl and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	17478-514	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	18 sections
COSOPT PF	HUMAN PRESCRIPTION DRUG LABEL	2	17478-604	SOLUTION/ DROPS	20 mg	OPHTHALMIC	NDA	18 sections
COSOPT	HUMAN PRESCRIPTION DRUG LABEL	2	17478-605	SOLUTION/ DROPS	20 mg	OPHTHALMIC	NDA	17 sections
Dorzolamide HCl	HUMAN PRESCRIPTION DRUG LABEL	1	24208-485	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	18 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	24208-486	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide Hydrochloride Ophthalmic Solution	HUMAN PRESCRIPTION DRUG LABEL	1	42571-141	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50090-1246	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	50090-1247	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide HCl	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2406	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	18 sections
Dorzolamide HCl	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2768	SOLUTION	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide HCl and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	50090-2867	SOLUTION	20 mg	OPHTHALMIC	ANDA	18 sections
Dorzolamide Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	50383-232	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	50383-233	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	50383-261	SOLUTION/ DROPS	20 mg	OPHTHALMIC	NDA	17 sections
Cosopt	HUMAN PRESCRIPTION DRUG LABEL	2	54868-4279	SOLUTION	20 mg	OPHTHALMIC	NDA	13 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5982	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	14 sections
Dorzolamide HCl	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6330	SOLUTION/ DROPS	22.30 mg	OPHTHALMIC	ANDA	13 sections
Dorzolamide and Timolol	HUMAN PRESCRIPTION DRUG LABEL	2	55545-1007	SOLUTION	20 mg	OPHTHALMIC	ANDA	1 sections
Dorzolamide hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	55545-1008	SOLUTION	20 mg	OPHTHALMIC	ANDA	1 sections
Dorzolamide Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	60429-114	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	60429-115	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	16 sections
DORZOLAMIDE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	61314-019	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide Hydrochloride and Timolol Maleate	HUMAN PRESCRIPTION DRUG LABEL	2	61314-030	SOLUTION	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	62332-519	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide Hydrochloride and Timolol Maleate Preservative Free	HUMAN PRESCRIPTION DRUG LABEL	2	65862-947	SOLUTION/ DROPS	20 mg	OPHTHALMIC	ANDA	17 sections
Dorzolamide hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	69315-304	SOLUTION	20 mg	OPHTHALMIC	ANDA	16 sections
Dorzolamide and Timolol	HUMAN PRESCRIPTION DRUG LABEL	2	69315-305	SOLUTION	20 mg	OPHTHALMIC	ANDA	16 sections
DORZOLAMIDE HYDROCHLORIDE and TIMOLOL MALEATE	HUMAN PRESCRIPTION DRUG LABEL	2	70069-051	SOLUTION	20 mg	OPHTHALMIC	ANDA	16 sections