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Pimecrolimus
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Name

Pimecrolimus

 EINECS 603-999-7
CAS No. 137071-32-0 Density 1.199 g/cm3
PSA 158.13000 LogP 5.65730
Solubility N/A Melting Point 135-136 °C
Formula C43H68ClNO11 Boiling Point 866.1 °C at 760 mmHg
Molecular Weight 810.466 Flash Point 477.572 °C
Transport Information N/A Appearance white crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 137071-32-0 (Pimecrolimus) Hazard Symbols N/A
Synonyms

33-epi-Chloro-33-desoxyascomycin;Elidel;SDZ ASM 981;UNII-7KYV510875;(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-3-((E)-2-((1R,3R,4S)-4-chloro-3-methoxycyclohexyl)-1-methylvinyl)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,26,26a-hexadecahydro-5,19-epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,17,20,21(4H,23H)-tetrone;

Article Data 7

Pimecrolimus Synthetic route

135635-46-0, 137767-76-1, 104987-12-4

ascomycin

137071-32-0

pimecrolimus

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; N-chloro-succinimide; triphenylphosphine In tetrahydrofuran at 39℃; Reagent/catalyst; Large scale;95%
Stage #1: ascomycin With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride In dichloromethane at -20℃; for 1h; Large scale;
Stage #2: With N-benzyl-N,N,N-triethylammonium chloride; lithium chloride In dichloromethane at 5 - 28℃; for 2h; Solvent; Temperature; Reagent/catalyst; Large scale;		89.1%
With pyridine; N-chloro-succinimide; triphenylphosphine In tetrahydrofuran at 20 - 65℃; for 6h;48.1%

C49H82ClNO11Si

A

23-dehydropimecrolimus

B

137071-32-0

pimecrolimus

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; dichloromethane at 20 - 25℃; for 72h;A 35%
B 46%
1178863-99-4

24-O-acetyl-pimecrolimus

137071-32-0

pimecrolimus

Conditions
ConditionsYield
With hydrogenchloride In methanol; water40%
148146-56-9

ascomycin 32-triflate

137071-32-0

pimecrolimus

Conditions
ConditionsYield
With lithium chloride In dichloromethane at -15 - 21℃; for 96h; Product distribution / selectivity;
With N-benzyl-N,N,N-triethylammonium chloride In toluene; acetonitrile at 0 - 25℃; Product distribution / selectivity;
67-56-1

methanol

137071-32-0

pimecrolimus

A

686773-65-9

C42H68ClNO10

B

686773-53-5

C44H72ClNO12

Conditions
ConditionsYield
at 5℃; Irradiation >360 nm;A 10%
B 66%
137071-32-0

pimecrolimus

A

686773-65-9

C42H68ClNO10

B

686773-59-1

C43H68ClNO11

C

C43H68ClNO11

Conditions
ConditionsYield
In acetonitrile at 5℃; for 15h; Irradiation >360 nm;A 3%
B 2%
C 38%

Pimecrolimus Specification

The Pimecrolimus is an organic compound with the formula C43H68ClNO11. The systematic name of this chemical is (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-3-{(1E)-1-[(1R,3R,4R)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl}-8-ethyl-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,1 7,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone. With the CAS registry number 137071-32-0, it is also named as 15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 3-[(E)-2-[(1R,3R,4R)-4-chloro-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,2. The product's categories are Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is an immunomodulating agent used in the treatment of atopic dermatitis (eczema).

Physical properties about Pimecrolimus are: (1)ACD/LogP: 5.76; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5; (4)ACD/LogD (pH 7.4): 5; (5)ACD/BCF (pH 5.5): 4264; (6)ACD/BCF (pH 7.4): 4253; (7)ACD/KOC (pH 5.5): 13799; (8)ACD/KOC (pH 7.4): 13762; (9)#H bond acceptors: 12; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 158.13 Å2; (13)Index of Refraction: 1.543; (14)Molar Refractivity: 213.029 cm3; (15)Molar Volume: 675.847 cm3; (16)Polarizability: 84.451×10-24cm3; (17)Surface Tension: 49.658 dyne/cm; (18)Density: 1.199 g/cm3; (19)Flash Point: 477.572 °C; (20)Enthalpy of Vaporization: 143.028 kJ/mol; (21)Boiling Point: 866.054 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl[C@@H]1CC[C@H](C[C@H]1OC)\C=C(/C)[C@H]2OC(=O)[C@@H]4CCCCN4C(=O)C(=O)[C@]3(O)O[C@H]([C@H](C[C@@H](C)CC(\C)=C\[C@@H](CC)C(=O)C[C@H](O)[C@H]2C)OC)[C@@H](OC)C[C@H]3C
(2)InChI: InChI=1/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31+,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
(3)InChIKey: KASDHRXLYQOAKZ-ZPSXYTITBN
(4)Std. InChI: InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31+,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
(5)Std. InChIKey: KASDHRXLYQOAKZ-ZPSXYTITSA-N

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