THALIDOMIDE, (S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H10N2O4
Molecular Weight	258.2295
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1N([C@H]2CCC(=O)NC2=O)C(=O)C3=C1C=CC=C3

InChI

InChIKey=UEJJHQNACJXSKW-VIFPVBQESA-N

InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11599654
Curator's Comment: The description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12175160 | https://www.ncbi.nlm.nih.gov/pubmed/15167912 | https://www.ncbi.nlm.nih.gov/pubmed/19297157

(s)-Thalidomide is an enantiomer of immunomodulatory agent Thalidomide. Thalidomide enantiomers are converted to each other in vivo, and Thalidomide contains both left and right-handed isomers in equal amounts. (s)-Thalidomide has proven efficacy in multiple myeloma. s-thalidomide-induced apoptosis associated with increases in I-kB activity, downregulation of NF-kB activity and an increase in Bax: Bcl-2 ratio. In cells cultured with s-thalidomide, there was a four-fold downregulation of the NFkB gene that was associated with a significant decrease in its protein activity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nuclear factor NF-kappa-B complex 11 Target ID: CHEMBL2094258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15167912	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Multiple myeloma 159 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf	Primary		Approved 8429	THALOMID Approved Use INDICATIONS AND USAGE. Thalomid in combination with dexamethasoneisindicated for the treatment of patients with newly diagnosedmultiple myeloma. Thalomid is indicated for the a cute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Thalomid is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date 1998
Erythema nodosum leprosum 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf	Primary		Approved 8429	THALOMID Approved Use INDICATIONS AND USAGE. Thalomid in combination with dexamethasoneisindicated for the treatment of patients with newly diagnosedmultiple myeloma. Thalomid is indicated for the a cute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Thalomid is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date 1998

PubMed

Title	Date	PubMed
A complementary systems account of word learning: neural and behavioural evidence.	2009 Dec 27	19933145

Patents

Sample Use Guides

In Vivo Use Guide

Multiple myeloma: 200 mg orally once daily. The recommended dose of dexamethasone is 40 mg/day on days 1-4, 9-12, and 17-20 every 28 days. Erythema nodosum leprosum (ENL): 100 to 300 mg/day for an episode of cutaneous ENL. Up to 400 mg/day for severe cutaneous Erythema nodosum leprosum.

Route of Administration: Oral

In Vitro Use Guide

To study the effect of s-thalidomide (Cellgene Corp, NJ, USA) on cell growth, the multiple myeloma cell line U266 was reset in fresh RPMI-1640 culture medium supplemented with s-thalidomide (0–1000 mkM) for 3 days. As s-thalidomide was reconstituted in DMSO, separate cultures of cells with equal amounts of DMSO were also set up as controls. Cell number, cell viability and cell cycle distribution were then assessed on day 3.

Name

Type

Language

THALIDOMIDE, (S)-

Common Name

English

S(-)-3-(3-AMINO-PHTHALIMIDO)-GLUTARAMIDE

Common Name

English

ENMD-0995

Code

English

(S)-(-)-THALIDOMIDE

Common Name

English

NSC-91730

Code

English

ENMD 0995

Code

English

THALIDOMIDE, (-)-

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

151701