clofazimine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	692	2030-63-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: lamprene clofazimine chlofazimine	A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619) Molecular weight: 473.40 Formula: C27H22Cl2N4 CLOGP: 7.55 LIPINSKI: 1 HAC: 4 HDO: 1 TPSA: 39.99 ALOGS: -5.50 ROTB: 4 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

lamprene
clofazimine
chlofazimine

A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619)

Molecular weight: 473.40
Formula: C27H22Cl2N4
CLOGP: 7.55
LIPINSKI: 1
HAC: 4
HDO: 1
TPSA: 39.99
ALOGS: -5.50
ROTB: 4

Status: OFM

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

Drug dosage:

Dose	Unit	Route
0.10	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.20 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	7.03 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	57 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Dec. 15, 1986	FDA	NOVARTIS

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
Electrocardiogram QT prolonged	463.91	28.31	172	4423	54416	56233056
Drug resistance	125.10	28.31	51	4544	20491	56266981
Neuropathy peripheral	102.52	28.31	77	4518	102816	56184656
Anaemia	93.84	28.31	112	4483	267399	56020073
Hepatotoxicity	89.93	28.31	46	4549	31107	56256365
Tuberculosis	79.71	28.31	31	4564	10998	56276474
Vomiting	76.09	28.31	141	4454	498087	55789385
Off label use	72.26	28.31	147	4448	556033	55731439
Optic neuropathy	71.96	28.31	19	4576	1941	56285531
Type 2 lepra reaction	70.04	28.31	10	4585	31	56287441
Skin hyperpigmentation	56.79	28.31	20	4575	5377	56282095
Mycobacterial infection	55.15	28.31	15	4580	1715	56285757
Polyneuropathy	55.02	28.31	25	4570	13025	56274447
Skin discolouration	53.75	28.31	34	4561	34322	56253150
Respiratory failure	52.99	28.31	51	4544	95011	56192461
Intentional product use issue	52.78	28.31	52	4543	99681	56187791
Drug reaction with eosinophilia and systemic symptoms	47.42	28.31	30	4565	30274	56257198
Myelosuppression	45.26	28.31	24	4571	17431	56270041
Product use in unapproved indication	44.38	28.31	56	4539	140766	56146706
Aspartate aminotransferase increased	43.56	28.31	43	4552	82559	56204913
Pulmonary tuberculosis	37.43	28.31	14	4581	4462	56283010
Alanine aminotransferase increased	33.95	28.31	40	4555	93622	56193850
Haemoptysis	33.53	28.31	23	4572	26537	56260935
Meningitis tuberculous	33.37	28.31	8	4587	552	56286920
Herbal toxicity	32.20	28.31	5	4590	31	56287441
Ototoxicity	32.05	28.31	9	4586	1157	56286315
Mycobacterium abscessus infection	31.88	28.31	8	4587	668	56286804
Drug-induced liver injury	30.31	28.31	24	4571	34438	56253034
Pathogen resistance	30.13	28.31	13	4582	5987	56281485
Tinnitus	28.76	28.31	22	4573	30020	56257452
Pyelonephritis chronic	28.32	28.31	6	4589	236	56287236

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
Electrocardiogram QT prolonged	575.02	26.77	220	4974	37767	31654383
Type 2 lepra reaction	273.43	26.77	48	5146	316	31691834
Tuberculosis	207.35	26.77	70	5124	8271	31683879
Hepatotoxicity	189.42	26.77	82	5112	19044	31673106
Neuropathy peripheral	126.15	26.77	102	5092	75547	31616603
Intentional product use issue	123.62	26.77	85	5109	49262	31642888
Off label use	105.20	26.77	196	4998	347078	31345072
Anaemia	68.65	26.77	124	5070	213398	31478752
Deafness	66.40	26.77	33	5161	10432	31681718
Ototoxicity	65.13	26.77	20	5174	1738	31690412
Drug resistance	64.83	26.77	43	5151	23410	31668740
Skin hyperpigmentation	62.37	26.77	22	5172	2949	31689201
Incorrect product administration duration	61.42	26.77	24	5170	4278	31687872
Type 1 lepra reaction	56.04	26.77	9	5185	31	31692119
Vomiting	49.09	26.77	111	5083	223862	31468288
Product use in unapproved indication	47.29	26.77	69	5125	99102	31593048
Nausea	42.20	26.77	128	5066	307819	31384331
Tinnitus	40.57	26.77	28	5166	16247	31675903
Optic neuropathy	40.41	26.77	14	5180	1779	31690371
Aspartate aminotransferase increased	39.53	26.77	50	5144	62669	31629481
Acoustic neuroma	37.55	26.77	8	5186	157	31691993
Drug-induced liver injury	36.60	26.77	31	5163	24332	31667818
Hypertriglyceridaemia	36.32	26.77	20	5174	7778	31684372
Lepromatous leprosy	36.08	26.77	7	5187	84	31692066
Myelosuppression	35.62	26.77	25	5169	14895	31677255
Optic neuritis	35.27	26.77	15	5179	3315	31688835
Deafness neurosensory	34.74	26.77	14	5180	2702	31689448
HIV infection	34.01	26.77	12	5182	1608	31690542
Polyneuropathy	33.86	26.77	23	5171	12999	31679151
Pulmonary tuberculosis	33.30	26.77	16	5178	4695	31687455
Blood sodium decreased	30.50	26.77	23	5171	15292	31676858
Toxic optic neuropathy	29.22	26.77	9	5185	789	31691361
Oral candidiasis	27.46	26.77	19	5175	11058	31681092
Mycobacterium abscessus infection	27.19	26.77	8	5186	600	31691550
Iridocyclitis	27.06	26.77	10	5184	1530	31690620

FDA Adverse Event Reporting System (Geriatric)

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
Electrocardiogram QT prolonged	964.29	21.52	379	9385	83138	70835542
Type 2 lepra reaction	338.51	21.52	57	9707	346	70918334
Hepatotoxicity	260.21	21.52	125	9639	43861	70874819
Neuropathy peripheral	254.00	21.52	178	9586	126718	70791962
Tuberculosis	208.40	21.52	78	9686	14770	70903910
Drug resistance	179.84	21.52	93	9671	38097	70880583
Off label use	167.53	21.52	335	9429	742725	70175955
Intentional product use issue	161.50	21.52	133	9631	120009	70798671
Anaemia	148.24	21.52	226	9538	403197	70515483
Optic neuropathy	109.60	21.52	33	9731	3200	70915480
Skin hyperpigmentation	104.21	21.52	38	9726	6677	70912003
Vomiting	103.92	21.52	242	9522	592869	70325811
Deafness	93.67	21.52	48	9716	19255	70899425
Polyneuropathy	88.98	21.52	48	9716	21367	70897313
Incorrect product administration duration	83.40	21.52	37	9727	10787	70907893
Ototoxicity	82.66	21.52	26	9738	2915	70915765
Myelosuppression	76.22	21.52	49	9715	30096	70888584
Type 1 lepra reaction	75.59	21.52	12	9752	47	70918633
Product use in unapproved indication	75.53	21.52	116	9648	207362	70711318
Aspartate aminotransferase increased	75.24	21.52	90	9674	126888	70791792
Skin discolouration	69.01	21.52	50	9714	37275	70881405
Tinnitus	63.57	21.52	47	9717	36129	70882551
Pulmonary tuberculosis	61.03	21.52	27	9737	7818	70910862
Mycobacterial infection	58.84	21.52	21	9743	3467	70915213
Optic neuritis	57.76	21.52	27	9737	8873	70909807
Drug-induced liver injury	56.90	21.52	53	9711	56060	70862620
Drug reaction with eosinophilia and systemic symptoms	55.40	21.52	53	9711	57960	70860720
Mycobacterium abscessus infection	51.71	21.52	15	9749	1277	70917403
Meningitis tuberculous	48.37	21.52	14	9750	1183	70917497
Lepromatous leprosy	48.35	21.52	9	9755	103	70918577
Alanine aminotransferase increased	46.12	21.52	77	9687	147403	70771277
Respiratory failure	46.11	21.52	83	9681	168652	70750028
Nausea	45.61	21.52	234	9530	851854	70066826
HIV infection	41.80	21.52	13	9751	1404	70917276
Toxic optic neuropathy	40.57	21.52	12	9752	1094	70917586
Pain	40.54	21.52	18	9746	628798	70289882
Hypokalaemia	40.35	21.52	68	9696	131120	70787560
Psychotic disorder	38.96	21.52	36	9728	37665	70881015
Haemoptysis	38.13	21.52	41	9723	51411	70867269
Hypertriglyceridaemia	36.96	21.52	22	9742	11789	70906891
Deafness neurosensory	36.59	21.52	18	9746	6614	70912066
Fall	35.03	21.52	9	9755	444087	70474593
Acoustic neuroma	34.56	21.52	8	9756	278	70918402
Pneumothorax	33.35	21.52	28	9736	25818	70892862
Hypoacusis	32.05	21.52	28	9736	27241	70891439
Treatment noncompliance	30.86	21.52	35	9729	46539	70872141
Bicytopenia	28.57	21.52	13	9751	4015	70914665
Cardiopulmonary failure	28.39	21.52	15	9749	6395	70912285
Malnutrition	28.28	21.52	23	9741	20294	70898386
Vestibular disorder	28.26	21.52	11	9753	2309	70916371
Transaminases increased	27.26	21.52	33	9731	46985	70871695
Decreased appetite	27.26	21.52	98	9666	304682	70613998
Electrolyte imbalance	26.50	21.52	25	9739	26836	70891844
Infective pulmonary exacerbation of cystic fibrosis	26.44	21.52	18	9746	12140	70906540
Blood sodium decreased	25.28	21.52	26	9738	30972	70887708
Oral candidiasis	24.19	21.52	23	9741	24929	70893751
Pyelonephritis chronic	24.18	21.52	6	9758	281	70918399
Tuberculoid leprosy	23.67	21.52	5	9759	113	70918567
Drug hypersensitivity	23.38	21.52	4	9760	262455	70656225
Steroid dependence	23.15	21.52	7	9757	688	70917992
Herbal toxicity	23.13	21.52	4	9760	29	70918651
Pathogen resistance	22.75	21.52	17	9747	13262	70905418
Poor feeding infant	22.67	21.52	5	9759	139	70918541
Hypomagnesaemia	22.64	21.52	28	9736	40736	70877944
Facial paralysis	22.59	21.52	20	9744	19788	70898892
Immune reconstitution inflammatory syndrome associated tuberculosis	21.92	21.52	7	9757	823	70917857

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J04BA01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF LEPRA Drugs for treatment of lepra
FDA EPC	N0000175483	Antimycobacterial
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:35816	leprostatic drugs
CHEBI has role	CHEBI:37958	dyes
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000893	Anti-Inflammatory Agents
MeSH PA	D007917	Leprostatic Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Pyoderma gangrenosum	indication	74578003	DOID:8553
Leprosy	indication	81004002	DOID:1024
Erythema nodosum leprosum	indication	240411003
Multibacillary leprosy	indication	416257001
Dapsone resistant leprosy	indication	416597004
Mycobacteriosis	off-label use	88415009
Nausea and vomiting	contraindication	16932000
Splenic infarction	contraindication	22996003	DOID:2533
Disorder of digestive system	contraindication	53619000	DOID:77
Diarrhea	contraindication	62315008
Gastrointestinal hemorrhage	contraindication	74474003
Gastrointestinal obstruction	contraindication	126765001
Disease of liver	contraindication	235856003	DOID:409
Breastfeeding (mother)	contraindication	413712001

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.81	Basic
pKa2	5.53	Basic
pKa3	2.07	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
Uncharacterized oxidoreductase CzcO-like	Enzyme		CZCO_GEOKA					WOMBAT-PK
Cruzipain	Enzyme		CYSP_TRYCR		IC50	5.22		CHEMBL

External reference:

ID	Source
4019504	VUID
N0000147624	NUI
D00278	KEGG_DRUG
203021	RXNORM
4019504	VANDF
C0008996	UMLSCUI
CHEBI:3749	CHEBI
CHEMBL1292	ChEMBL_ID
D002991	MESH_DESCRIPTOR_UI
DB00845	DRUGBANK_ID
9184	IUPHAR_LIGAND_ID
2248	INN_ID
D959AE5USF	UNII
2794	PUBCHEM_CID
1685	MMSL
4473	MMSL
d01121	MMSL
003007	NDDF
387410004	SNOMEDCT_US
72924009	SNOMEDCT_US

Pharmaceutical products:

None