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Rimiducid

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ACTIVE PHARMA INGREDIENTS

3 API Suppliers, 3 USDMF

3 API Suppliers
3 USDMF

DEVELOPMENTS

17 Drugs in Development

17 Drugs in Development

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Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Ap1903, 195514-63-7, Ap-1903, Rimiducid [inn], Ap 1903, H564l1w5j2

Molecular Formula

C₇₈H₉₈N₄O₂₀

Molecular Weight

1411.6 g/mol

InChI Key

GQLCLPLEEOUJQC-ZTQDTCGGSA-N

FDA UNII

H564L1W5J2

Rimiducid is a lipid-permeable tacrolimus analogue with homodimerizing activity. Dimerizer drug AP1903 homodimerizes an analogue of human protein FKBP12 (Fv) which contains a single acid substitution (Phe36Val) so that AP1903 binds to wild-type FKBP12 with 1000-fold lower affinity. This agent is used to homodimerize the Fv-containing drug-binding domains of genetically engineered receptors such as the iCD40 receptor of the autologous dendritic cell vaccine BP-GMAX-CD1, resulting in receptor activation.

1 2D Structure

Rimiducid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R)-3-(3,4-dimethoxyphenyl)-1-[3-[2-[2-[[2-[3-[(1R)-3-(3,4-dimethoxyphenyl)-1-[(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carbonyl]oxypropyl]phenoxy]acetyl]amino]ethylamino]-2-oxoethoxy]phenyl]propyl] (2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carboxylate

2.1.2 InChI

InChI=1S/C78H98N4O20/c1-13-57(53-43-67(93-7)73(97-11)68(44-53)94-8)75(85)81-37-17-15-25-59(81)77(87)101-61(31-27-49-29-33-63(89-3)65(39-49)91-5)51-21-19-23-55(41-51)99-47-71(83)79-35-36-80-72(84)48-100-56-24-20-22-52(42-56)62(32-28-50-30-34-64(90-4)66(40-50)92-6)102-78(88)60-26-16-18-38-82(60)76(86)58(14-2)54-45-69(95-9)74(98-12)70(46-54)96-10/h19-24,29-30,33-34,39-46,57-62H,13-18,25-28,31-32,35-38,47-48H2,1-12H3,(H,79,83)(H,80,84)/t57-,58-,59-,60-,61+,62+/m0/s1

2.1.3 InChI Key

GQLCLPLEEOUJQC-ZTQDTCGGSA-N

2.1.4 Canonical SMILES

CCC(C1=CC(=C(C(=C1)OC)OC)OC)C(=O)N2CCCCC2C(=O)OC(CCC3=CC(=C(C=C3)OC)OC)C4=CC(=CC=C4)OCC(=O)NCCNC(=O)COC5=CC=CC(=C5)C(CCC6=CC(=C(C=C6)OC)OC)OC(=O)C7CCCCN7C(=O)C(CC)C8=CC(=C(C(=C8)OC)OC)OC

2.1.5 Isomeric SMILES

CC[C@@H](C1=CC(=C(C(=C1)OC)OC)OC)C(=O)N2CCCC[C@H]2C(=O)O[C@H](CCC3=CC(=C(C=C3)OC)OC)C4=CC(=CC=C4)OCC(=O)NCCNC(=O)COC5=CC=CC(=C5)[C@@H](CCC6=CC(=C(C=C6)OC)OC)OC(=O)[C@@H]7CCCCN7C(=O)[C@@H](CC)C8=CC(=C(C(=C8)OC)OC)OC

2.2 Other Identifiers

2.2.1 UNII

H564L1W5J2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-piperidinecarboxylic Acid, 1-((2s)-1-oxo-2-(3,4,5-trimethoxyphenyl)butyl)-, 2,2'-(1,2-ethanediylbis(imino(2-oxo-2,1-ethanediyl)oxy-3,1-phenylene((1r)-3-(3,4-dimethoxyphenyl)propylidene))) Ester, (2s,2's)-

2. Ap 1903 Reagent

3. Ap1903

2.3.2 Depositor-Supplied Synonyms

1. Ap1903

2. 195514-63-7

3. Ap-1903

4. Rimiducid [inn]

5. Ap 1903

6. H564l1w5j2

7. [(1r)-3-(3,4-dimethoxyphenyl)-1-[3-[2-[2-[[2-[3-[(1r)-3-(3,4-dimethoxyphenyl)-1-[(2s)-1-[(2s)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carbonyl]oxypropyl]phenoxy]acetyl]amino]ethylamino]-2-oxoethoxy]phenyl]propyl] (2s)-1-[(2s)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carboxylate

8. (1r,1'r)-((((ethane-1,2-diylbis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(oxy))bis(3,1-phenylene))bis(3-(3,4-dimethoxyphenyl)propane-1,1-diyl) (2s,2's)-bis(1-((s)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate)

9. 2-piperidinecarboxylic Acid, 1-((2s)-1-oxo-2-(3,4,5-trimethoxyphenyl)butyl)-, 2,2'-(1,2-ethanediylbis(imino(2-oxo-2,1-ethanediyl)oxy-3,1-phenylene((1r)-3-(3,4-dimethoxyphenyl)propylidene))) Ester, (2s,2's)-

10. Unii-h564l1w5j2

11. Ap 1903 Reagent

12. Rimiducid (usan/inn)

13. Rimiducid [usan:inn]

14. Rimiducid [usan]

15. Rimiducid (ap1903)

16. Ap 1903new

17. Rimiducid [who-dd]

18. Chembl269259

19. Schembl10111062

20. Dtxsid80173226

21. Ex-a1711

22. Vha51463

23. Ap1903ap1903

24. S9726

25. Cs-3162

26. Db04974

27. Ac-35487

28. Hy-16046

29. D11195

30. A919658

31. Q27279658

32. (1r,1'r)-((((ethane-1,2-diylbis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(oxy))bis(3,1-phenylene))bis(3-(3,4-dimethoxyphenyl)propane-1,1-diyl)(2s,2's)-bis(1-((s)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate)

33. 2-piperidinecarboxylic Acid, 1-(1-oxo-2-(3,4,5-trimethoxyphenyl)butyl)-, 1,2-ethanediylbis(imino(2-oxo-2,1-ethanediyl)oxy-3,1-phenylene(3-(3,4-dimethoxyphenyl)propylidene)) Ester, (2s-(1(r*),2r*(s*(s*(1(r*),2r*)))))-

2.4 Create Date

2007-07-04

3 Chemical and Physical Properties

Molecular Formula	C₇₈H₉₈N₄O₂₀
Molecular Weight	1411.6 g/mol
XLogP3	11.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	39
Exact Mass	1410.67744153 g/mol
Monoisotopic Mass	1410.67744153 g/mol
Topological Polar Surface Area	262 Å²
Heavy Atom Count	102
Formal Charge	0
Complexity	2330
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in bone marrow transplant and graft versus host disease.

Treatment of graft versus host disease

5 Pharmacology and Biochemistry

5.1 Pharmacology

Rimiducis is used to activate inducible caspase-9 produced by a modified gene included in some CAR T-cell therapies. This activation produces rapid induction of apoptosis in activated modified T-cells and resolution of the signs and symptoms of graft versus host disease within 24 hours.

5.2 Mechanism of Action

Rimiducid binds to a drug binding domain derived from human FK506-binding protein which is present on a modified form of inducible caspase-9. This binding results in dimerization and subsequent activation of caspase-9. This system was designed to function as a "safety switch" in CAR T-cell therapy used in hematological cancers. Retroviral vectors used in production of these modified cells preferentially integrate this gene nearby promoters associated with T-cell activation. This results in higher expression of the modified inducible caspase-9 product in activated T-cells. In practice, this allows for specific targeting of these active T-cells by rimiducid which results in a decrease in circulating cell numbers of over 90% in the setting of graft versus host disease. This specificity spares non-alloreactive T-cells and allows for successful reconstitution of the transplanted immune system from these cells.[24753538] Additionally, these non-alloreactive cells retain their sensitivity to rimiducid.

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