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

Stem definition	Drug id	CAS RN
antineoplastics, nucleotoxic agents	1820	53-19-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: mitotane chloditan chlodithane lysodren mitotan opeprim	A derivative of the insecticide DICHLORODIPHENYLDICHLOROETHANE that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression. Molecular weight: 320.03 Formula: C14H10Cl4 CLOGP: 6.06 LIPINSKI: 1 HAC: 0 HDO: 0 TPSA: ALOGS: -7.53 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

mitotane
chloditan
chlodithane
lysodren
mitotan
opeprim

A derivative of the insecticide DICHLORODIPHENYLDICHLOROETHANE that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression.

Molecular weight: 320.03
Formula: C14H10Cl4
CLOGP: 6.06
LIPINSKI: 1
HAC: 0
HDO: 0
TPSA:
ALOGS: -7.53
ROTB: 3

Status: OFP

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

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	40 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
April 28, 2004	EMA	HRA Pharma Rare Diseases
July 8, 1970	FDA	BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

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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
Adrenal insufficiency	113.41	51.00	31	1036	17884	63470071
Febrile neutropenia	59.29	51.00	32	1035	118417	63369538
Drug clearance increased	57.50	51.00	8	1059	125	63487830
Adrenocortical carcinoma	56.36	51.00	7	1060	42	63487913

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FDA Adverse Event Reporting System (Male)

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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
Adrenal insufficiency	95.37	41.43	25	496	14022	34942388
Adrenocortical carcinoma	59.78	41.43	7	514	27	34956383

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FDA Adverse Event Reporting System (Geriatric)

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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
Adrenal insufficiency	185.25	48.51	52	1509	28435	79714392
Adrenocortical carcinoma	95.53	48.51	12	1549	67	79742760
Febrile neutropenia	58.85	48.51	43	1518	230956	79511871
Drug clearance increased	57.99	48.51	9	1552	261	79742566
Neutropenia	54.65	48.51	45	1516	287665	79455162

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01XX23	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS OTHER ANTINEOPLASTIC AGENTS Other antineoplastic agents
FDA MoA	N0000185506	Cytochrome P450 3A4 Inducers
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D018931	Antineoplastic Agents, Hormonal

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

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Disease	Relation	SNOMED_ID	DOID
Carcinoma in situ of adrenal cortex	indication	92526009
Hypercortisolism	off-label use	47270006
Shock	contraindication	27942005
Disease of liver	contraindication	235856003	DOID:409
Adrenal cortical hypofunction	contraindication	386584007	DOID:10493
Breastfeeding (mother)	contraindication	413712001
Traumatic injury	contraindication	417746004
CNS Toxicity	contraindication

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Cytochrome P450 11B1, mitochondrial	Enzyme	P15538	C11B1_HUMAN	INHIBITOR			WOMBAT-PK	CHEMBL
Cholesterol side-chain cleavage enzyme, mitochondrial	Enzyme	P05108	CP11A_HUMAN	INHIBITOR			CHEMBL	CHEMBL
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	6.09	DRUG MATRIX
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.51	DRUG MATRIX
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.19	DRUG MATRIX
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	5.56	DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		Ki	5.38	DRUG MATRIX
Adrenodoxin, mitochondrial	Unclassified	P10109	ADX_HUMAN				WOMBAT-PK
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	6.10	DRUG MATRIX
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	5.80	DRUG MATRIX

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External reference:

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ID	Source
002669	NDDF
1449	MMSL
204257	RXNORM
2597	INN_ID
26288002	SNOMEDCT_US
4018140	VUID
4018140	VANDF
404865004	SNOMEDCT_US
4211	PUBCHEM_CID
5123	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Lysodren	HUMAN PRESCRIPTION DRUG LABEL	1	76336-080	TABLET	500 mg	ORAL	NDA	24 sections
Lysodren	HUMAN PRESCRIPTION DRUG LABEL	1	76336-080	TABLET	500 mg	ORAL	NDA	24 sections

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