Oxacyclohexane open ring tacrolimus
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| Category | Tacrolimus Analogue Set |
| Catalog number | BBF-05769 |
| CAS | 144432-23-5 |
| Molecular Weight | 822.03 |
| Molecular Formula | C44H71NO13 |
| Purity | ≥90% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-05769 | 5 mg | $1099 | In stock |
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Oxacyclohexane open ring tacrolimus is an impurity of Tacrolimus, which is a macrolide drug that is widely used as a potent immunosuppressant.
Specification
| Related CAS | 1393890-33-9 (Tacrolimus open ring) |
| Synonyms | Tacrolimus Open Ring Impurity; Tacrolimus related compound, tacrolimus open ring; 3H-Pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,19,21(4H,8H,12H,23H)-tetrone, 5,6,11,13,14,15,16,17,18,20,24,25,26,26a-tetradecahydro-5,15,20,20-tetrahydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)-; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)-5,6,11,13,14,15,16,17,18,20,24,25,26,26a-Tetradecahydro-5,15,20,20-tetrahydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,19,21(4H,8H,12H,23H)-tetrone; 3H-Pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,19,21(4H,8H,20H,23H)-tetrone, 5,6,11,12,13,14,15,16,17,18,24,25,26,26a-tetradecahydro-5,15,20,20-tetrahydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, [3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,26aR*]]- |
| IUPAC Name | (5R,7S,8R,9S,11S,13E,15R,18S,19R,20S,23S)-3,3,8,18-tetrahydroxy-20-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-7,9-dimethoxy-5,11,13,19-tetramethyl-15-prop-2-enyl-21-oxa-1-azabicyclo[21.4.0]heptacos-13-ene-2,4,16,22-tetrone |
| Canonical SMILES | CC1CC(C(C(CC(C(=O)C(C(=O)N2CCCCC2C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC3CCC(C(C3)OC)O)C)(O)O)C)OC)O)OC |
| InChI | InChI=1S/C44H71NO13/c1-10-13-31-19-25(2)18-26(3)20-37(56-8)39(49)38(57-9)22-28(5)41(50)44(53,54)43(52)45-17-12-11-14-32(45)42(51)58-40(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)55-7/h10,19,21,26,28-34,36-40,46-47,49,53-54H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+/m0/s1 |
| InChI Key | NDOLMJWSFDJWBE-SICKWUOOSA-N |
Properties
| Boiling Point | 933.9±65.0 °C at 760 mmHg |
| Density | 1.20±0.1 g/cm3 |
Reference Reading
1. Tacrolimus successfully used to control refractory eosinophilic granulomatosis with polyangiitis complicated by invasive aspergillosis and chronic hepatitis B.
Hirano F1,2, Mizoguchi F1, Harigai M1,2, Miyasaka N1, Kohsaka H1. Int J Rheum Dis. 2016 Apr 29. doi: 10.1111/1756-185X.12869. [Epub ahead of print]
While several alternatives to cyclophosphamide have been proposed for refractory eosinophilic granulomatosis with polyangiitis (EGPA), therapeutic options are limited in patients with chronic infections. We report a case of refractory EGPA complicated by invasive aspergillosis and chronic hepatitis B. Although multiple immunosuppressants, including cyclophosphamide, were not effective, tacrolimus was used successfully to control disease without exacerbating concomitant infections in the long term. Tacrolimus could be an alternative choice in the treatment of EGPA, especially when aggressive immunosuppression is unfeasible.
2. After Intestinal Transplantation Kidney Function Is Impaired by Downregulation of Epithelial Ion Transporters in the Ileum.
Reiner J1, Hsieh CJ2, Straarup C3, Bodammer P3, Schäffler H3, Graepler F2, Stüker D4, Kratt T4, Linnebacher M5, Nadalin S4, Witte M6, Königsrainer A4, Lamprecht G7. Transplant Proc. 2016 Mar;48(2):499-506. doi: 10.1016/j.transproceed.2015.12.068.
BACKGROUND: Intestinal transplantation is a treatment option for intestinal failure. Although nephrotoxic medication after transplantation is a major cause for posttransplant renal insufficiency, it remains unclear why kidney dysfunction is particularly frequent after intestinal transplantation.
3. Reduced-dose methotrexate in combination with tacrolimus was associated with rapid engraftment and recovery from oral mucositis without affecting the incidence of GVHD.
Matsukawa T1, Hashimoto D2, Sugita J2, Nakazawa S3, Matsushita T3, Kashiwazaki H3, Goto H2, Onozawa M2, Kahata K2, Fujimoto K2, Endo T2, Kondo T2, Hashino S4, Yamazaki Y3, Teshima T2. Int J Hematol. 2016 Apr 27. [Epub ahead of print]
Allogeneic hematopoietic stem cell transplantation is a curable treatment for hematological diseases. Graft-versus-host disease (GVHD) causes morbidity and mortality after HSCT. Methotrexate (MTX) is used for GVHD prophylaxis, but its appropriate dose remains unclear. In the present study, we compared the efficacy and toxicity of 15-10-10 MTX (day +1: 15 mg/m2; days +3 and +6: 10 mg/m2) with 10-7-7 MTX (day +1: 10 mg/m2; day +3 and +6: 7 mg/m2) in combination with tacrolimus. The cumulative incidence rates of grades II-IV acute GVHD, grades III-IV acute GVHD and chronic GVHD in the 15-10-10 MTX and 10-7-7 MTX groups did not differ to a statistically significant extent. The median time for neutrophil engraftment in the 15-10-10 MTX group was 16 days (range, 11-31 days), while that in the 10-7-7 group was 15 days (range, 12-19 days) (P = 0.024). Moreover, the median time for platelet recovery was significantly shorter in the 10-7-7 MTX group (22 days; range, 13-49 days) than that in the 15-10-10 MTX group (27 days; range, 9-405 days) (P = 0.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
