RIMIDUCID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C78H98N4O20
Molecular Weight	1411.6275
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C(=O)N1CCCC[C@H]1C(=O)O[C@H](CCC2=CC(OC)=C(OC)C=C2)C3=CC(OCC(=O)NCCNC(=O)COC4=CC=CC(=C4)[C@@H](CCC5=CC(OC)=C(OC)C=C5)OC(=O)[C@@H]6CCCCN6C(=O)[C@@H](CC)C7=CC(OC)=C(OC)C(OC)=C7)=CC=C3)C8=CC(OC)=C(OC)C(OC)=C8

InChI

InChIKey=GQLCLPLEEOUJQC-ZTQDTCGGSA-N

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

HIDE SMILES / InChI

Molecular Formula	C78H98N4O20
Molecular Weight	1411.6275
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9724721 | https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=640440 | http://www.bellicum.com/technology/caspacide/ | https://www.ncbi.nlm.nih.gov/pubmed/26072403 | http://www.bellicum.com/product-candidates/bpx-501/ | http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2016/06/WC500209180.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21383499 | https://www.ncbi.nlm.nih.gov/pubmed/11222367

Rimiducid (AP1903) is a lipid-permeable tacrolimus analogue with homodimerizing activity. Rimiducid homodimerizes an analogue of human protein FKBP12 (Fv) which contains a single acid substitution (Phe36Val). This agent is used to homodimerize the Fv-containing drug-binding domains of genetically engineered proteins such as the iCD40 receptor, Fas intracellular domain or iCaspase 9 resulting in downstream signaling activation during cell therapy. Orphan designation was granted for rimiducid (AP1903) for the treatment of graft-versus-host disease.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
FK506-binding protein 1A 9 Target ID: CHEMBL1902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9724721	Binding Agent 1064		1.8 nM [IC50]
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9724721	Activator 1430		0.1 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Graft-versus-host disease 3 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2016/06/WC500209180.pdf http://www.bellicum.com/product-candidates/bpx-501/ https://www.ncbi.nlm.nih.gov/pubmed/11222367 https://www.ncbi.nlm.nih.gov/pubmed/22047558 https://www.ncbi.nlm.nih.gov/pubmed/25977584	Primary		Phase II 1132	Unknown Approved Use Unknown
Hematologic malignancies 19 Sources: http://adisinsight.springer.com/drugs/800033916 http://www.bellicum.com/product-candidates/bpx-501/ http://www.bellicum.com/technology/caspacide/	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1273 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504275	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RIMIDUCID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2972 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504275	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RIMIDUCID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11504275	1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RIMIDUCID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 mg/kg single, intravenous Dose: 1 mg/kg Route: intravenous Route: single Dose: 1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11504275 Page: p.873	healthy, ADULT n = 4 Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/11504275 Page: p.873	Other AEs: Vasodilatation... Other AEs: Vasodilatation (25%) Sources: https://pubmed.ncbi.nlm.nih.gov/11504275 Page: p.873

AEs

AE	Significance	Dose	Population
Vasodilatation	25%	1 mg/kg single, intravenous Dose: 1 mg/kg Route: intravenous Route: single Dose: 1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/11504275 Page: p.873	healthy, ADULT n = 4 Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/11504275 Page: p.873

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00ABFT	https://www.aablocks.com/goods/Goods/detail?id=AA00ABFT
AbMole Bioscience	M10066	http://www.abmole.com/products/ap1903.html
Achemtek	0102-014219	http://www.achemtek.com/195514-63-7
Adooq BioScience	A13519	https://www.adooq.com/ap1903.html
Ambinter	Amb24106497	http://www.ambinter.com/reference/24106497
Aurum Pharmatech LLC	Z-3163	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_3163
BLD Pharm	BD630505	http://www.bldpharm.com/products/195514-63-7.html
BioCrick	BCC5361	http://www.biocrick.com/AP1903-BCC5361.html
CSNpharm	CSN18073	https://www.csnpharm.com/products/ap1903.html
Chem Scene	CS-3162	http://www.chemscene.com/195514-63-7.html
Chemspace	CSSS00161189521	https://chem-space.com/CSSS00161189521
Excenen	EX-A1711	http://www.excenen.com/searchresultlist.php?id=195514-63-7
Lab Network	LN01341918	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341918
MedChem Express	HY-16046	https://www.medchemexpress.com/AP1903.html
MolPort	MolPort-046-417-123	https://www.molport.com/shop/molecule-link/MolPort-046-417-123
MuseChem	I002495	https://www.musechem.com/product/I002495.html
eNovation Chemicals	D672698	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672698

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Twenty-eight normal healthy male volunteers were randomized into five dosage groups of AP1903 (0.01, 0.05, 0.1, 0.5, and 1 mg/kg)

Route of Administration: Intravenous

In Vitro Use Guide

The human fibrosarcoma line HT1080 was engineered to express stably a fusion protein comprising a myristoylation sequence, two copies of F36V-FKBP, and the human Fas intracellular domain. Rimiducid (AP1903) elicited potent and dose-dependent apoptotic death of these engineered cells in culture, with an EC50 of ~0.1 nM

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:02:14 UTC 2023` Edited by `admin` on `Sat Dec 16 02:02:14 UTC 2023`
Record UNII	H564L1W5J2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIMIDUCID

Official Name

English

rimiducid [INN]

Common Name

English

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)-

Common Name

English

AP1903

Code

English

Rimiducid [WHO-DD]

Common Name

English

RIMIDUCID [USAN]

Common Name

English

AP-1903

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

126299