1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene

• ChemBase ID: 530
• Molecular Formular: C14H10Cl4
• Molecular Mass: 320.0412
• Monoisotopic Mass: 317.95366104
• SMILES: ClC(Cl)C(c1ccc(Cl)cc1)c1c(Cl)cccc1
• Canonical SMILES: ClC(C(c1ccccc1Cl)c1ccc(cc1)Cl)Cl
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene; 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
• IUPAC Traditional name: mitotane; 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
• Brand Name: Chloditan; Chlodithan; Chlodithane; Khlodithan; Lysodren; Mitotan; Mitotanum [INN-Latin]
• Synonyms: Mitotane; o,p′-DDD; (2,4′-Dichlorodiphenyl)dichloroethane; Mitotane; 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; 1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; 2,4′-DDD; 1,1-Dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane solution; 2,4′-DDD solution; 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene; o,p′-DDD; o,p'-DDD, CB-313, Lysodren,1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane; 氯苯二氯乙烷; 米托坦; 1-(2-氯苯基)-1-(4-氯苯基)-2,2-二氯乙烷; 1-(2-氯苯基)-1-(4-氯苯基)-2,2-二氯乙烷; 1,1-二氯-2-(2-氯苯基)-2-(4-氯苯基)乙烷 溶液; 2,4′-DDD 溶液

Database IDs

• CAS Number: 53-19-0; 184475-35-2
• EC Number: 200-659-6; 200-166-6
• MDL Number: MFCD00000850
• Beilstein Number: 2056007
• PubChem SID: 24899277; 160963993; 24855696; 24861830; 24872530; 24869452; 24892859; 46508319
• PubChem CID: 4211
• ATC CODE: L01XX23
• CHEMBL: 1670
• Chemspider ID: 4066
• DrugBank ID: DB00648
• KEGG ID: D00420
• Unique Ingredient Identifier: 78E4J5IB5J
• Wikipedia Title: Mitotane
• Medline Plus: a608050

CALCULATED PROPERTIES

JChem

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.110365
• LogD (pH = 7.4): 6.110365
• Log P: 6.110365
• Molar Refractivity: 79.9654 cm^3
• Polarizability: 30.937008 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.08
• LOG S: -7.53
• Solubility (Water): 9.42e-06 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 mg/L; Methanol
• Apperance: Crystalline Solid
• Melting Point: 76-78 °C; 76-87°C; 77 - 78°C
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): 6; 6.06

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KH7880000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 40
• Safety Statements: 36/37; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H351
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 40%
• Half Life: 18 to 159 days
• Protein Bound: 6%
• Legal Status: Rx-only
• Pregnancy Category: C
• US Licence: MITOTANE
• Gene Information: rat ... Ar(24208)

Product Information

• Purity: ≥98% (HPLC); ≥99%; 95%
• Concentration: 100 ng/μL in methanol
• Grade: analytical standard; for diagnostic uses (cancer investigation); PESTANAL®, analytical standard
• Packaging: ampule of 1000 mg; ampule of 250 mg
• Linear Formula: (ClC6H4)2CHCHCl2

DETAILS

DrugBank - DB00648

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For treatment of inoperable adrenocortical tumours; Cushing's syndrome
• Pharmacology: Mitotane is an oral chemotherapeutic agent indicated in the treatment of inoperable adrenal cortical carcinoma of both functional and nonfunctional types. Mitotane can best be described as an adrenal cytotoxic agent, although it can cause adrenal inhibition, apparently without cellular destruction. The administration of Mitotane alters the extra-adrenal metabolism of cortisol in man; leading to a reduction in measurable 17-hydroxy corticosteroids, even though plasma levels of corticosteroids do not fall. The drug apparently causes increased formation of 6-B-hydroxyl cortisol.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and renal
• Absorption: About 40% oral Lysodren is absorbed
• Half Life: 18-159 days
• Protein Binding: 6%
• Elimination: A variable amount of metabolite (1%-17%) is excreted in the bile and the balance is apparently stored in the tissues.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 25925

Packaging
1 g in glass bottle

Sigma Aldrich - C63804

Packaging
10 g in glass bottle

Sigma Aldrich - 45836

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 35485

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - M372500

An Antineoplastic. Used as an adrenolytic agent.

REFERENCES

• Das, S., and Thomas, P.: Endocrinology, 140, 1953 (1999)
• Andersen, A., et al.: Ther. Drug. Monit., 21, 355 (1999)
• Leblond, V.S., and Hontela, T.: Toxicol. Appl. Pharmacol., 157, 16 (1999)