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Clarithromycin
Tier C — Watch / tradeClarithromycin
Taisho Pharmaceutical Holdings Co Ltd
Originator
1991
First approval
-
Expiry (public)
No sales data
Peak sales
Small molecule
Type
Targets：50S ribosomal subunit
Brand：Naxy, Klaricid, Macladin, Klacid, Biaxin, Clarino-500, Clarimax, Cyllind, Clarith, Veclam, Biaxin XL, Minebase
Indications (approved)：Sinusitis, Tonsillitis, Acute bronchitis, Chronic bronchitis, Lower respiratory tract infection, Pharyngitis, Infectious disease, Pneumonia
Regional status
US
Phase II
1999-11-02
EU
Phase III
2000-04-01
China
Approved
1996-01-01
Japan
Approved
1991-03-29
Factories producing this API1
Factories registered as producing this API in our sourcing network (RFQ records + product master), sorted by RFQ activity; the snapshot carries no cost or customer data.
1 producing factories on file — sign in to view the named list (factory details are not shown to guests).
Sign in to view factories →Synthetic routes & intermediates8 routes
Originator routes × 0Optimised (non-patent) × 7Process routes × 1
Routes are ordered originator first, then optimised / process (non-patent) routes; each lists steps, overall yield and the intermediate table (code / CAS / name) — ready for supplier sourcing and RFQ. Rendered by this site from structured data; no third-party route graphics used.
OptimisedRoute 1Steps 3 · Total yield 6g(Clarithromycin (Free))
Clarithromycin-001—Clarithromycin-002—Clarithromycin-003—API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-001 | - | benzyl (2S,3R,4S,6R)-4-{[(benzyloxy)carbonyl](methyl)amino}-2-{[(3R,4S,5S,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-6-methyloxan-3-yl carbonate |
| Clarithromycin-002 | - | benzyl (2S,3R,4S,6R)-4-{[(benzyloxy)carbonyl](methyl)amino}-2-{[(3R,4S,5S,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-1-oxacyclotetradecan-6-yl]oxy}-6-methyloxan-3-yl carbonate |
| Clarithromycin-003 | - | (3R,4S,5S,6R,7S,9R,11R,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-6-{[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione |
OptimisedRoute 3Steps 4 · Total yield 18g(Clarithromycin (Free))
Clarithromycin-006133445-26-8Clarithromycin-007887125-82-8Clarithromycin-008—Clarithromycin-009—Clarithromycin-010—Clarithromycin-011133415-69-7API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-006 | 133445-26-8 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydrpyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime] |
| Clarithromycin-007 | 887125-82-8 | Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-008 | - | Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-009 | - | Benzoic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-010 | - | Acetic acid (2S,3R,4S,6R)-4-(dimethylamino)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-10-[[(1-isopropoxycyclohexyl)oxy]imino]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-011 | 133415-69-7 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(1-isopropoxycyclohexyl)oxime] |
OptimisedRoute 4Steps 5 · Total yield 4.2g(Clarithromycin (Free))
Clarithromycin-01213127-18-9Clarithromycin-013611-19-8Clarithromycin-014206997-62-8Clarithromycin-0151395892-49-5Clarithromycin-016—Clarithromycin-017—Clarithromycin-018—Clarithromycin-019149882-99-5API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-012 | 13127-18-9 | (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
| Clarithromycin-013 | 611-19-8 | 2-Chlorobenzyl chloride |
| Clarithromycin-014 | 206997-62-8 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-7,12,13-trihydroxy-4- [(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime] |
| Clarithromycin-015 | 1395892-49-5 | Acetic acid (2S,3R,4S,6R)-2-[((3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yl)oxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-016 | - | Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-017 | - | Acetic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[(2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-018 | - | Benzoic acid (2S,3R,4S,6R)-2-[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-10-[[2-chlorobenzyloxy]imino]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxooxacyclotetradecan-6-yloxy]-4-(dimethylamino)-6-methyltetrahydropyran-3-yl ester |
| Clarithromycin-019 | 149882-99-5 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydropyran-2-yloxy]-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydropyran-2-yloxy]-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione 10-[O-(2-chlorobenzyl)oxime] |
OptimisedRoute 5Steps 1 · Total yield /
Clarithromycin-01213127-18-9API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-012 | 13127-18-9 | (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
OptimisedRoute 6Steps 5 · Total yield 17.5g(Clarithromycin (Free))
Clarithromycin-0207704-67-8Clarithromycin-01213127-18-9Clarithromycin-02113127-18-9Clarithromycin-022926-66-9Clarithromycin-023—Clarithromycin-0241253181-38-2Clarithromycin-02574-88-4Clarithromycin-02674-83-9Clarithromycin-0271253181-39-3API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-020 | 7704-67-8 | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione thiocyanate |
| Clarithromycin-012 | 13127-18-9 | Thiocyanic acid--(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy]-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one (1/1) |
| Clarithromycin-021 | 13127-18-9 | (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
| Clarithromycin-022 | 926-66-9 | 2-Ethoxyprop-1-ene |
| Clarithromycin-023 | - | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy]-10-[[(2-ethoxypropan-2-yl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy]-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one |
| Clarithromycin-024 | 1253181-38-2 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-([(2S,3R,4S,6R)-4-(Dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-10-[[(2-ethoxypropan-2-yl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-([(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
| Clarithromycin-025 | 74-88-4Available | Methyl iodide |
| Clarithromycin-026 | 74-83-9 | Bromomethane |
| Clarithromycin-027 | 1253181-39-3 | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-([(2S,3R,4S,6R)-4-(Dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-10-[[(2-ethoxypropan-2-yl)oxy]imino]-14-ethyl-12,13-dihydroxy-7-methoxy-4-([(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
OptimisedRoute 7Steps 2 · Total yield 52g(Clarithromycin-028)
Clarithromycin-01213127-18-9Clarithromycin-022926-66-9Clarithromycin-023—Clarithromycin-028—API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-012 | 13127-18-9 | (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
| Clarithromycin-022 | 926-66-9 | 2-Ethoxyprop-1-ene |
| Clarithromycin-023 | - | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy]-10-[[(2-ethoxypropan-2-yl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy]-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one |
| Clarithromycin-028 | - | (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy]-10-[[(2-ethoxypropan-2-yl)oxy]imino]-14-ethyl-7,12,13-trihydroxy-4-([(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]oxan-2-yl]oxy)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one |
OptimisedRoute 8Steps 1 · Total yield 88g(Clarithromycin-012)
Clarithromycin-0207704-67-8Clarithromycin-01213127-18-9API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-020 | 7704-67-8 | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione thiocyanate |
| Clarithromycin-012 | 13127-18-9 | (3R,4S,5S,6R,7R,9R,10Z,11S,12R,13S,14R)-6-[[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-14-ethyl-7,12,13-trihydroxy-10-(hydroxyimino)-4-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one |
ProcessRoute 2Steps 2 · Total yield 429.768g(Clarithromycin (Free))
Clarithromycin-004—Clarithromycin-005—API · Clarithromycin
| Code | CAS No. | Intermediate |
|---|---|---|
| Clarithromycin-004 | - | (2R,3R,4R,5R,6R,8R,9E,10S,11R,12R,13S)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]oxan-2-yl]oxy}-13-ethyl-6,11,12-trihydroxy-3-{[(4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]oxan-2-yl]oxy}-9-{[(2-methoxypropan-2-yl)oxy]imino}-2,4,6,8,10,12-hexamethylcyclotetradecan-1-one |
| Clarithromycin-005 | - | (2R,3R,4R,5R,6R,8R,9E,10S,11R,12R,13S)-5-{[(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-[(trimethylsilyl)oxy]oxan-2-yl]oxy}-13-ethyl-11,12-dihydroxy-6-methoxy-3-{[(4R,5S,6S)-4-methoxy-4,6-dimethyl-5-[(trimethylsilyl)oxy]oxan-2-yl]oxy}-9-{[(2-methoxypropan-2-yl)oxy]imino}-2,4,6,8,10,12-hexamethylcyclotetradecan-1-one |
Frequently asked questions
What are the approved indications of Clarithromycin?
Approved indications include: Sinusitis, Tonsillitis, Acute bronchitis, Chronic bronchitis, Lower respiratory tract infection, Pharyngitis, Infectious disease, Pneumonia.
When does the Clarithromycin patent expire?
No public expiry year is available for Clarithromycin yet; this page updates once verified.
How many synthesis routes are recorded for Clarithromycin?
8 synthesis routes are recorded; the shortest is 1 steps with / total yield. Intermediates in each route carry codes and CAS numbers.
Where can I buy Clarithromycin intermediates?
1 intermediate CAS of Clarithromycin are available through the Unibest supply network — see the route tables on this page and request a quote per CAS.
How do I get a quote for Clarithromycin intermediates?
Open the CAS profile of the target intermediate from this page, or submit an RFQ directly — the CAS enters the matching flow automatically and the supply network responds with quotes.
Source: cross-verified data (structured fields only) · 2026-09-29