Drug Details

General Information of the Drug (ID: DR7618)
Name
Mitotane
Synonyms
mitotane; 53-19-0; Mitotan; Lysodren; Chloditan; o,p'-DDD; Chlodithane; Khlodithan; Chlodithan; 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; 2,4'-Ddd; Mitotano; 1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene; NCI-C04933; o,p'-TDE; 2,4'-Dichlorodiphenyldichloroethane; 1-Chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)benzene; o,p'-Dichlorodiphenyldichloroethane; Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-; 2,4'-Dichlorophenyldichlorethane; CB 313; NSC 38721; 1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane; 2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane; 2-(o-Chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloroethane; 1,1-Dichloro-2,2-bis(2,4'-dichlorophenyl)ethane; NSC38721; 1,1-Dichloro-2-(p-chlorophenyl)-2-(o-chlorophenyl)ethane; 2,2-Bis(2-chlorophenyl-4-chlorophenyl)-1,1-dichloroethane; CB-313; NSC-38721; 2,4'-DDD;o,p'-DDD; Ethane, 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)-; Ethane, 2-(o-chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloro-; Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-; MFCD00000850; Mitotanum [INN-Latin]; o,p-Tde; NCGC00015226-07; 1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene; Mitotanum; DSSTox_CID_372; Mitotano [INN-Spanish]; DSSTox_RID_75548; DSSTox_GSID_20372; 2,4'-(2,2-dichloroethane-1,1-diyl)bis(chlorobenzene); Opeprim; 2,4 -Dichlorodiphenyldichloroethane; Mitotane (Lsodren); CB313; DDD, o,p'-; CAS-53-19-0; Lysodren (TN); SMR000326696; CCRIS 4397; HSDB 3240; SR-01000075751; EINECS 200-166-6; (o,p)-DDD; Mitotane (JAN/USP/INN); BRN 2056007; AI3-07575; Prestwick_75; Ethane,1-dichloro-; Mitotane (Lysodren); Mitotane [USAN:USP:INN:BAN:JAN]; (2,4'-Dichlorodiphenyl)dichloroethane; PubChem14974; Spectrum_001959; DDD-o,p'; (+-)-1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane; Spectrum2_000916; Spectrum3_000869; Spectrum4_000709; Spectrum5_002060; C 3010; (o,p')-DDD; SCHEMBL4040; CHEMBL1670; Lopac0_000251; WLN: GYGYR BG&R DG; BSPBio_002517; KBioGR_001237; KBioSS_002513; SPECTRUM330082; MLS001335899; MLS001335900; MLS002152914; MLS002153233; DivK1c_000703; SPBio_000792; CHEBI:6954; GTPL6957; Mitotane, >=98% (HPLC); DTXSID9020372; 2,4'-DDD, analytical standard; HMS502D05; KBio1_000703; KBio2_002505; KBio2_005073; KBio2_007641; KBio3_002017; NINDS_000703; HMS1923K19; HMS2091E07; HMS2232C16; HMS3260D04; HMS3369H10; HMS3655G06; HMS3715H07; HMS3869F13; Pharmakon1600-00330082; BCP11663; 2,4 inverted exclamation marka-DDD; Tox21_110103; Tox21_302804; Tox21_500251; CCG-40014; NSC755849; s1732; 1,2-bis(2,4'-dichlorophenyl)ethane; AKOS006028802; Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-, (+-)-; Tox21_110103_1; CS-1500; DB00648; LP00251; MCULE-2068358149; NSC-755849; SDCCGSBI-0050239.P006; IDI1_000703; NCGC00015226-02; NCGC00015226-03; NCGC00015226-04; NCGC00015226-05; NCGC00015226-06; NCGC00015226-08; NCGC00015226-09; NCGC00015226-10; NCGC00015226-11; NCGC00015226-12; NCGC00091374-01; NCGC00091374-02; NCGC00091374-03; NCGC00091374-04; NCGC00091374-05; NCGC00091374-06; NCGC00256452-01; NCGC00260936-01; 2,4'-DDD 10 microg/mL in Cyclohexane; AK546750; AS-11690; HY-13690; NCI60_003688; 2,4'-DDD 100 microg/mL in Cyclohexane; SBI-0050239.P004; AB0010565; EU-0100251; FT-0605518; ST51016017; SW199619-3; EN300-37268; 2,4 inverted exclamation marka-DDD;o,p'-DDD; 2,4'-DDD, PESTANAL(R), analytical standard; D00420; W-5031; AB00052337-09; AB00052337_10; 000M850; Q417465; SR-01000075751-1; SR-01000075751-3; SR-01000075751-6; Z425389592; 1-(o-Chlorophenyl)-1-(p-chlorophenyl)-2,2-dichloroethane; 1-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-2-chlorobenzene; Ethane,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)-; 1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene #; Mitotane, United States Pharmacopeia (USP) Reference Standard; Ethane, 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)- (8CI); 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane, analytical standard; o,p'-DDD; ; ; 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; ; ; Mitotane; 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane for diagnostic uses (cancer investigation), >=98% (HPLC); 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane, for diagnostic uses (cancer investigation), >=98% (HPLC)
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Molecular Type
Small molecule
Disease Adrenocortical carcinoma [ICD-11: 2D11] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absorption
The oral absorption of drug is 40%
Half-life
The concentration or amount of drug in body reduced by one-half in 18 - 159 days
Metabolism
The drug is metabolized via the hepatic
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C14H10Cl4
PubChem CID
4211
Canonical SMILES
C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)C(Cl)Cl)Cl
InChI
1S/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H
InChIKey
JWBOIMRXGHLCPP-UHFFFAOYSA-N
CAS Number
CAS 53-19-0
ChEBI ID
CHEBI:6954
TTD Drug ID
D0Z5OE
DrugBank ID
DB00648
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Polymyxin B      Bacillus polymyxa     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Acinetobacter baumannii ATCC 17978 Microorganism model Acinetobacter baumannii
Acinetobacter baumannii ATCC 19606 Microorganism model Acinetobacter baumannii
Acinetobacter baumannii FADDI-AB225 Microorganism model Acinetobacter baumannii
Acinetobacter baumannii FADDI-AB065 Microorganism model Acinetobacter baumannii
                    Experimental
                    Result(s)		 The disruption of the citric acid cycle and inhibition of nucleotide biogenesis are the key metabolic features associated with synergistic bacterial killing by the combination against polymyxin-susceptible and -resistant A. baumannii.
Target and Pathway
Target(s) Estrogen receptor (ESR)  Molecule Info  [3]
KEGG Pathway Estrogen signaling pathway Click to Show/Hide
2 Prolactin signaling pathway
3 Thyroid hormone signaling pathway
4 Endocrine and other factor-regulated calcium reabsorption
5 Proteoglycans in cancer
NetPath Pathway FSH Signaling Pathway Click to Show/Hide
2 EGFR1 Signaling Pathway
3 RANKL Signaling Pathway
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Signaling events mediated by HDAC Class II
3 Plasma membrane estrogen receptor signaling
4 LKB1 signaling events
5 Regulation of Telomerase
6 ATF-2 transcription factor network
7 AP-1 transcription factor network
8 FOXM1 transcription factor network
9 Validated nuclear estrogen receptor alpha network
10 Signaling mediated by p38-alpha and p38-beta
11 FOXA1 transcription factor network
Reactome Nuclear signaling by ERBB4 Click to Show/Hide
2 Nuclear Receptor transcription pathway
WikiPathways Estrogen signaling pathway Click to Show/Hide
2 Nuclear Receptors Meta-Pathway
3 Estrogen Receptor Pathway
4 Signaling by ERBB4
5 JAK/STAT
6 Integrated Pancreatic Cancer Pathway
7 Leptin signaling pathway
8 miR-targeted genes in muscle cell - TarBase
9 Integrated Breast Cancer Pathway
10 Nuclear Receptors
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6957).
Reference 2 Synergistic Killing of Polymyxin B in Combination With the Antineoplastic Drug Mitotane Against Polymyxin-Susceptible and -Resistant Acinetobacter baumannii: A Metabolomic Study. Front Pharmacol. 2018 Apr 16;9:359.
Reference 3 Mitotane for adrenocortical carcinoma treatment. Curr Opin Investig Drugs. 2005 Apr;6(4):386-94.
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