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Chemistry

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Also known as: Symproic, Naldemedine tosilate, Naldemedine tosylate [usan], Naldemedine (tosylate), V1n8f1rvvo, 1345728-04-2
Molecular Formula
C39H42N4O9S
Molecular Weight
742.8  g/mol
InChI Key
WCYDLROFMZJJLE-RTMHEQJQSA-N
FDA UNII
V1N8F1RVVO

Naldemedine Tosylate
1 2D Structure

Naldemedine Tosylate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(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;4-methylbenzenesulfonic acid
2.1.2 InChI
InChI=1S/C32H34N4O6.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39);2-5H,1H3,(H,8,9,10)/t22-,26+,31+,32-;/m1./s1
2.1.3 InChI Key
WCYDLROFMZJJLE-RTMHEQJQSA-N
2.1.4 Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)O.CC(C)(C1=NC(=NO1)C2=CC=CC=C2)NC(=O)C3=C(C4C56CCN(C(C5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8)O
2.1.5 Isomeric SMILES
CC1=CC=C(C=C1)S(=O)(=O)O.CC(C)(C1=NC(=NO1)C2=CC=CC=C2)NC(=O)C3=C([C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8)O
2.2 Other Identifiers
2.2.1 UNII
V1N8F1RVVO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 17-(cyclopropylmethyl)-6,7-didehydro-4,5alpha-epoxy-3,6,14-trihydroxy-n-(2-(3-phenyl- 1,2,4-oxadiazol-5-yl)propan-2-yl)morphinan-7-carboxamide

2. Naldemedine

3. S-297995

4. Symproic

2.3.2 Depositor-Supplied Synonyms

1. Symproic

2. Naldemedine Tosilate

3. Naldemedine Tosylate [usan]

4. Naldemedine (tosylate)

5. V1n8f1rvvo

6. 1345728-04-2

7. Unii-v1n8f1rvvo

8. Symproic (tn)

9. Chembl3039508

10. Schembl20720003

11. Dtxsid10158809

12. Naldemedine Tosylate [mi]

13. Naldemedine Tosylate (jan/usan)

14. Naldemedine Tosilate [jan]

15. Hy-19627a

16. Naldemedine Tosilate [who-dd]

17. Naldemedine Tosylate [orange Book]

18. Cs-0030916

19. D10478

20. Q27291424

21. 17-(cyclopropylmethyl)-6,7-didehydro-4,5a-epoxy-3,6,14-trihydroxy-n-(2-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-2-yl)morphinan-7-carboxamide 4-methylbenzenesulfonic Acid

22. 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)-,(5.alpha.)-, 4-methylbenzenesulfonate (1:1)

23. 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)-, 4-methylbenzenesulfonate (1:1)

2.4 Create Date
2012-03-19
3 Chemical and Physical Properties
Molecular Weight 742.8 g/mol
Molecular Formula C39H42N4O9S
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass742.26725010 g/mol
Monoisotopic Mass742.26725010 g/mol
Topological Polar Surface Area204 Ų
Heavy Atom Count53
Formal Charge0
Complexity1340
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 1  
Drug NameSYMPROIC
Active IngredientNALDEMEDINE TOSYLATE
CompanySHIONOGI INC (Application Number: N208854. Patents: 9108975, RE46365, RE46375)

4.2 Drug Indication

Rizmoic is indicated for the treatment of opioid-induced constipation (OIC) in adult patients who have previously been treated with a laxative.


Treatment of opioid-induced constipation (OIC)


5 Pharmacology and Biochemistry
5.1 ATC Code

A06AH05


API SUPPLIERS

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Shandong Loncom Pharmaceutical

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Virtual BoothShandong Loncom is an R&D-focused manufacturer of Anti-cancer APIs.

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USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT
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NDC API

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NALDEMEDINE TOSYLATE

NDC Package Code : 53044-002

Start Marketing Date : 2017-03-23

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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Listed Suppliers

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Virtual BoothShandong Loncom is an R&D-focused manufacturer of Anti-cancer APIs.

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Naldemedine Tosylate

About the Company : Established in May 2012, Shandong Loncom Pharmaceutical operates as a fully owned subsidiary of Shandong Bestcomm Pharmaceutical Co., Ltd. Situated in the Qihe Economic Development...

Established in May 2012, Shandong Loncom Pharmaceutical operates as a fully owned subsidiary of Shandong Bestcomm Pharmaceutical Co., Ltd. Situated in the Qihe Economic Development Zone, Shandong Province, Shandong Loncom has operational API pilot tests and production bases adhering to international standards. With 13 production lines dedicated to oral solid preparations, oral liquid preparations and API, it is actively expanding its preparation workshops for small-volume injections, soft capsules, eye drops, topical medicines and innovative drug R&D centres.
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Drugs in Development

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Details:

Based on Phase 3 trial data, Rizmoic has been shown to increase the frequency of bowel movements compared to placebo in patients either with cancer or chronic non-cancer pain who had previously received laxative treatment.


Lead Product(s): Naldemedine Tosylate

Therapeutic Area: Gastroenterology Brand Name: Rizmoic

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Shionogi

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable September 30, 2020

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Sandoz B2B

Switzerland
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euroPLX 86 Munich
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Details : Based on Phase 3 trial data, Rizmoic has been shown to increase the frequency of bowel movements compared to placebo in patients either with cancer or chronic non-cancer pain who had previously received laxative treatment.

Brand Name : Rizmoic

Molecule Type : Small molecule

Upfront Cash : Not Applicable

September 30, 2020

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FDF Dossiers

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euroPLX 86 Munich
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NALDEMEDINE TOSYLATE

Brand Name : SYMPROIC

Dosage Form : TABLET;ORAL

Dosage Strength : EQ 0.2MG BASE

Packaging :

Approval Date : 2017-03-23

Application Number : 208854

Regulatory Info : RX

Registration Country : USA

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FDA Orange Book

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NALDEMEDINE TOSYLATE

Brand Name : SYMPROIC

Dosage Form : TABLET;ORAL

Dosage Strength : EQ 0.2MG BASE

Approval Date : 2017-03-23

Application Number : 208854

RX/OTC/DISCN : RX

RLD : Yes

TE Code :

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Patents & EXCLUSIVITIES

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US Patents

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NALDEMEDINE TOSYLATE

US Patent Number : RE46375

Drug Substance Claim : Y

Drug Product Claim : Y

Application Number : 208854

Patent Use Code : U-1185

Delist Requested :

Patent Use Description : TREATMENT OF OPIOID-IN...

Patent Expiration Date : 2026-10-05

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NALDEMEDINE TOSYLATE

US Patent Number : RE46365

Drug Substance Claim : Y

Drug Product Claim : Y

Application Number : 208854

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-01-11

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NALDEMEDINE TOSYLATE

US Patent Number : 9108975

Drug Substance Claim : Y

Drug Product Claim : Y

Application Number : 208854

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2031-11-11

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BDSI

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NALDEMEDINE TOSYLATE

US Patent Number : 10952968

Drug Substance Claim : Y

Drug Product Claim : Y

Application Number : 208854

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-05-13

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