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

Molecular Formula	C13H10N2O4
Molecular Weight	258.2295
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Multiple myeloma 159 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf	Primary		Approved 8583	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 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
0.93 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10933131/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:		THALIDOMIDE, (S)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.23 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10933131/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:		THALIDOMIDE, (R)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7702998/	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	THALIDOMIDE, (S)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.75 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10933131/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THALIDOMIDE, (S)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.42 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10933131/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:	THALIDOMIDE, (R)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7702998/	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	THALIDOMIDE, (R)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7702998/	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		THALIDOMIDE, (S)- blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
34% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9499573/			THALIDOMIDE, (S)- plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 CYP2E1 1060 CYP1A2 2153 CYP2C19 2057 P-gp 1741	P-gp 2052 CYP2C19 1119 CYP3A5 446	P-gp 301

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNjEyMyJ9fQ==	inconclusive [IC50 19.9526 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNjEyMyJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNjEyMyJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNjEyMyJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDI2MTIzIn19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQyNjEyMyJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDI2MTIzIn19	no [IC50 >10 uM]
P-gp 1932	inducer 1966 Sources: https://link.springer.com/article/10.1007/s00280-005-0087-3	no
P-gp 1932	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s00280-005-0087-3	no

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00280-005-0087-3	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20443640/	yes
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20443640/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22382316/	yes	yes (pharmacogenomic study) Comment: The AUC of (S)-thalidomide were 1.64 and 2.46μg·h/L for hetEM and PM, respectively. Sources: https://pubmed.ncbi.nlm.nih.gov/22382316/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDI2MTIzIn19

PubMed

Title	Date	PubMed
A complementary systems account of word learning: neural and behavioural evidence.	2009-12-27	19933145
European Academy of Paediatrics, Barcelona, Spain, October 7-10, 2006. Abstracts.	2006-11	17242961
Effects of neonatal intensive care on girls' and boys' language development.	2003	12725539
Effects of thalidomide, cytochrome P-450 and TNF-alpha on angiogenesis in a three-dimensional collagen gel-culture.	2002-10	12484444
[Ovarian hyperstimulation syndrome in preterm infants].	2002-08-29	12198593

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:08:14 GMT 2025` Edited by `admin` on `Mon Mar 31 21:08:14 GMT 2025`
Record UNII	TG87FSR590
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THALIDOMIDE, (S)-

Common Name

English

ENMD 0995

Preferred Name

English

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

Common Name

English

ENMD-0995

Code

English

(S)-(-)-THALIDOMIDE

Common Name

English

NSC-91730

Code

English

THALIDOMIDE, (-)-

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

151701