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53-19-0 molecular structure
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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 and InChIs

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

Cite this record

CBID:530 http://www.chembase.cn/molecule-530.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
24892859
24861830
160963993
24855696
46508319
24872530
24869452
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 6.110365  LogD (pH = 7.4) 6.110365 
Log P 6.110365  Molar Refractivity 79.9654 cm3
Polarizability 30.937008 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 6.08  LOG S -7.53 
Solubility (Water) 9.42e-06 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 mg/L expand Show data source
Methanol expand Show data source
Apperance
Crystalline Solid expand Show data source
Melting Point
76-78 °C expand Show data source
76-87°C expand Show data source
77 - 78°C expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
Hydrophobicity(logP)
6 expand Show data source
6.06 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
KH7880000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1230 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
40 expand Show data source
Safety Statements
36/37 expand Show data source
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H301-H311-H331-H370 expand Show data source
H351 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
P281 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US) expand Show data source
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 expand Show data source
RID/ADR
UN 1230 3/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
40% expand Show data source
Half Life
18 to 159 days expand Show data source
Protein Bound
6% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C expand Show data source
US Licence
MITOTANE expand Show data source
Gene Information
rat ... Ar(24208) expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥99% expand Show data source
95% expand Show data source
Concentration
100 ng/μL in methanol expand Show data source
Grade
analytical standard expand Show data source
for diagnostic uses (cancer investigation) expand Show data source
PESTANAL®, analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
ampule of 1000 mg expand Show data source
ampule of 250 mg expand Show data source
Linear Formula
(ClC6H4)2CHCHCl2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00648 external link
Item Information
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 external link
Packaging
1 g in glass bottle
Sigma Aldrich - C63804 external link
Packaging
10 g in glass bottle
Sigma Aldrich - 45836 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Sigma Aldrich - 35485 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Toronto Research Chemicals - M372500 external link
An Antineoplastic. Used as an adrenolytic agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

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