NALDEMEDINE

ID: ALA2105755

Chembl Id: CHEMBL2105755

Cas Number: 916072-89-4

PubChem CID: 54732242

Max Phase: Approved

First Approval: 2017

Molecular Formula: C32H34N4O6

Molecular Weight: 570.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Naldemedine | S-297995 | S-297995 | NALDEMEDINE|916072-89-4|UNII-03KSI6WLXH|03KSI6WLXH|S-297995|Naldemedine [USAN:INN]|S 297995|S-297,995|(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,7,9-trihydroxy-N-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl]-1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-6-carboxamide|Morphinan-7-carboxamide, 17-(cyclopropylmethyl)-6,7-didehydro-4,5-epoxy-3,6,14- trihydroxy-N-(1-methyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)-,(5alpha)-|compound 9k (PMID: 304Show More⌵

Synonyms from Alternative Forms(4): Naldemedine tosilate | Rizmoic | Symproic | Naldemedine tosylate

Canonical SMILES:  CC(C)(NC(=O)C1=C(O)[C@@H]2Oc3c(O)ccc4c3[C@@]23CCN(CC2CC2)[C@H](C4)[C@]3(O)C1)c1nc(-c2ccccc2)no1

Standard InChI:  InChI=1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1

Standard InChI Key:  AXQACEQYCPKDMV-RZAWKFBISA-N

Alternative Forms

1. Parent:

   

   ALA2105755

   NALDEMEDINE

2. Alternative Forms:

   

   ALA2105755

   Naldemedine tosylate

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 570.65

Molecular Weight (Monoisotopic): 570.2478

AlogP: 3.48

#Rotatable Bonds: 6

Polar Surface Area: 141.18

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.77

CX Basic pKa: 9.05

CX LogP: 2.43

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.35

Np Likeness Score: 0.29

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Unpublished dataset, 

3. WHO Anatomical Therapeutic Chemical Classification, 

4. Inagaki M, Kume M, Tamura Y, Hara S, Goto Y, Haga N, Hasegawa T, Nakamura T, Koike K, Oonishi S, Kanemasa T, Kai H..  (2019)  Discovery of naldemedine: A potent and orally available opioid receptor antagonist for treatment of opioid-induced adverse effects.,  29  (1): [PMID:30446313] [10.1016/j.bmcl.2018.11.007]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification