LEVAMLODIPINE BESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H25ClN2O5.C6H6O3S
Molecular Weight	567.051
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C2=C(COCCN)NC(C)=C([C@@H]2C3=C(Cl)C=CC=C3)C(=O)OC

InChI

InChIKey=ZPBWCRDSRKPIDG-LMOVPXPDSA-N

InChI=1S/C20H25ClN2O5.C6H6O3S/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21;7-10(8,9)6-4-2-1-3-5-6/h5-8,17,23H,4,9-11,22H2,1-3H3;1-5H,(H,7,8,9)/t17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C20H25ClN2O5
Molecular Weight	408.876
Charge	0
Count

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

Molecular Formula	C6H6O3S
Molecular Weight	158.175
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24683248 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/019787s047lbl.pdf | https://www.drugs.com/international/levamlodipine.html

Levalmodipine (S-amlodipine) is an active enantiomer of amlodipine, a calcium antagonist that inhibits the transmembrane influx of calcium ions into vascular smooth muscle and cardiac muscle. Experimental data suggest that S-amlodipine binds to both dihydropyridine and nondihydropyridine binding sites. The contractile processes of cardiac muscle and vascular smooth muscle are dependent upon the movement of extracellular calcium ions into these cells through specific ion channels. S-Amlodipine inhibits calcium ion influx across cell membranes selectively, with a greater effect on vascular smooth muscle cells than on cardiac muscle cells. Enantiomerically pure S-amlodipine is marketed in some countries worldwide, while racemate, containing active S-enantiomer an inactive R-enantiomer is marketed in the USA and indicated for the treatment of hypertension and coronary artery disease.

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
2.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN	TELMISARTAN	LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
147.43 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN	TELMISARTAN	LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
161.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
45.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29559771/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: TELMISARTAN	TELMISARTAN	LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17213004/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		LEVAMLODIPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP3A 214 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2E1 882 CYP1A2 1524	CYP3A 191 CYP3A5 395 CYP1A2 1054 CYP2B6 664 CYP2C8 693 P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	no [IC50 >50 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	no [IC50 >50 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	no [IC50 >50 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	no [IC50 >50 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	yes [IC50 40.12 uM]
CYP2C8 965	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	yes [IC50 9.55 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	yes [Ki 21.45 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	yes [Ki 7.22 uM]
CYP3A 298	inhibitor 3277 Sources: https://www.mdpi.com/1420-3049/22/11/1879 Page: -	yes [Ki 8.95 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	unlikely
CYP2B6 664	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	unlikely
CYP2C8 693	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	unlikely
CYP2D6 1217	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	unlikely
CYP3A 191	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/212895Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	yes
CYP3A4 1737	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	yes
CYP3A5 395	substrate 3367 Sources: https://dmd.aspetjournals.org/content/42/2/245 Page: -	yes
P-gp 1537	substrate 3367 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2006.02733.x Page: -	yes	yes (pharmacogenomic study) Comment: Amlodipine pharmacokinetics was affected by the genetic polymorphisms of the ABCB1 gene in humans. Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2006.02733.x Page: -

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00324Y	https://www.aablocks.com/goods/Goods/detail?id=AA00324Y
Aaron Chemicals	AR0032WQ	http://www.aaronchem.com/103129-82-4
Achemtek	0104-007429	http://www.achemtek.com/103129-82-4
Adooq BioScience	A14935	https://www.adooq.com/s-amlodipine.html
Ambeed	A707253	https://www.ambeed.com/products/103129-82-4.html
Angene	AGN-PC-0OS68B	http://www.angenechemical.com/productshow/AGN-PC-0OS68B.html
ApexBio Technology	B1410	http://www.apexbt.com/amlodipine.html
AvaChem Scientific	1626	http://www.avachem.com/productSearch.asp?1626
AvaChem Scientific	1626B	http://www.avachem.com/productSearch.asp?1626B
BLD Pharm	BD41113	http://www.bldpharm.com/products/103129-82-4.html
BioChemPartner	BCP22052	http://www.biochempartner.com/103129-82-4-BCP22052
BioSynth	Q-101935	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-101935.html
CSNpharm	CSN27383	https://www.csnpharm.com/products/levamlodipine.html
Chem Scene	CS-0003533	http://www.chemscene.com/103129-82-4.html
ChemMol	44015596	http://www.chemmol.com/chemmol/44015596.html
Chemspace	CSSB00016998253	https://chem-space.com/CSSB00016998253
DC Chemicals	DC9122	http://www.dcchemicals.com/product_show-_S_Amlodipine.html
Lab Network	LN01273625	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01273625
MedChem Express	HY-14744	https://www.medchemexpress.com/levamlodipine.html
MuseChem	R011077	https://www.musechem.com/product/R011077.html
OChem	10811	http://www.ocheminc.com/index.php?act=psearch&pid=129A824
Parchem	81464	https://www.parchem.com/chemical-supplier-distributor/S-amlodipine-081464.aspx
Selleck Chemicals	S3674	http://www.selleckchem.com/products/levamlodipine.html
Smolecule	S532909	http://www.smolecule.com/products/s532909
THE BioTek	bt-273307	https://www.thebiotek.com/product/inhibitors/bt-273307
abcr GmbH	AB564502	http://www.abcr.com/shop/en/AB564502
iChemical	EBD32703	http://www.ichemical.com/products/103129-82-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Tolerability and effectiveness of (S)-amlodipine compared with racemic amlodipine in hypertension: a systematic review and meta-analysis.	2010 Feb	24683248

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:00:10 UTC 2023` Edited by `admin` on `Sat Dec 16 11:00:10 UTC 2023`
Record UNII	885H5YC40L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVAMLODIPINE BESYLATE

Common Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-1,4-DIHYDRO-6-METHYL-, 3-ETHYL 5-METHYL ESTER, (4S)-, MONOBENZENESULFONATE

Common Name

English

(S)-AMLODIPINE BESYLATE

Common Name

English

LEVAMLODIPINE BESILATE

Common Name

English

Levamlodipine besilate [WHO-DD]

Common Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 2-((2-AMINOETHOXY)METHYL)-4-(2-CHLOROPHENYL)-1,4-DIHYDRO-6-METHYL-, 3-ETHYL 5-METHYL ESTER, (4S)-, BENZENESULFONATE (1:1)

Systematic Name

English

(-)-AMLODIPINE BESYLATE

Common Name

English

Code System Code Type Description

PUBCHEM

11365087